How you can resist funding the government → other tax resistance strategies → frugality / simple living / self-sufficiency → FIRE (financial independence, retire early)

While I’ve been studying my Aristotle, links have been piling up in my bookmarks. Here are some of them:

A new documentary film called The Pacifist is doing the festival circuit. It concerns war tax resister Larry Bassett, his large act of income tax resistance and redirection, and his attempts to provoke the U.S. government to respond to his stand. It features interviews of Bassett, interspersed with historical footage from government propaganda films encouraging people to pay their taxes to keep the war machine going, and with a collage of contemporary news footage about American militarism. It does a good job of helping you get to know Bassett better and to learn about the history of his pacifism and his war tax resistance stand.
Speaking of documentaries, I thought this article on five lessons I learned while making a documentary film about FIRE (the “financial independence, retire early” community) was very interesting.
Finland evidently publishes the taxable income of every citizen as a public record that any busybody can browse through. Do you suppose more or fewer people would resist their taxes if such a practice were typical? Ruth Benn considers issues of taxation, privacy, and openness about our finances at NWTRCC’s blog.
Senator Rand Paul has published his Annual Festivus Report of federal government waste. Just the thing to infuriate some people about how their hard-earned taxes are spent. If that doesn’t do the trick, check out this map showing the 40% of the world’s nations in which the U.S. military is engaged in “counterterrorism” operations.
Conscientious objector Halil Karapasiaoglou of Turkish Cyprus was convicted of evading the military draft. He vowed to go to jail rather than pay the fine.
Some encouraging numbers here:

Because of the repeated [budget] cuts, the IRS has drastically stopped pursuing “nonfilers” who do not submit their tax returns. The number of investigations into nonfilers fell from 2.4 million in 2011 to 362,000 in 2017. The agency has also drastically reduced its investigations of filers who do not pay their tax debts. In 2010, the IRS let $482 million in old tax debt lapse, but by 2017, that number increased to $8.3 billion.

It’s something of a golden age of tax evasion.
Hey look: Another “suspicious package” evacuates an IRS building.
The federal government “shutdown” is also taking its toll on the IRS. At a time of year when the agency is usually bulking up its temporary workforce and preparing for income tax filing season, instead it’s sending most of its workforce home, and making the rest work without pay. Protests by employees are planned, and there’s also a lawsuit in the works that claims forcing the agency workers to work without pay violates labor laws.
“From the executive leadership of top weapons-makers, to the senior government officials designing and purchasing the nation’s military arsenal, the United States’ national defense hierarchy is, for the first time, largely run by women.”
And: “CIA Director Gina Haspel has appointed another woman to the top level of the agency, naming Cynthia ‘Didi’ Rapp as deputy director for analysis, essentially the top analyst in the CIA. The appointment means that the top three directorates of the agency, for operations, analysis, and science and technology are now all headed by women.”
Boy am I looking forward to all of the peace and justice I was promised would happen once that bad ol’ patriarchy got smashed.
A family in Alberta has refused to pay the carbon tax portion of their heating bill in protest against broken promises from the government.
The epidemic of speed camera destruction continues worldwide:
This is especially widespread now in France, thanks to the gilets jaunes protests:
- Yellow vests are the latest fashion trend for French speed cameras
- There are no longer any functioning radars on the roads of Vaucluse after the last of them were burned
- All of the radars on the Toulouse ring road have been disabled
- 60% of the radars in Grand Reims were taken out
- 50 radars vandalized in le Cher
- 23 of the 33 radars in the Tarn are out of service
- 21 out of 22 in Puy-de-Dôme no longer ticket drivers
- All five of the radars in Pays-Haut are now monuments to direct action
- “Almost all” of the radars in the Loire are out of service. The article seems to indicate that the government has stopped trying to repair them since they get vandalized again so soon.
- A radar on the RD 9 became the tenth burned in Haute-Loire in recent months
- Two more Alsatian radars, five in Vaucluse, one in Yzeux, another in Ploudaniel, four in the Rethélois, three in Pluneret, Ploeren, and Theix-Noyalo, and three more in Lapalisse were put to the torch in December
- Three radars were taken out in Cambrésis, one in Cayenne, and five in Martinique
- Radar cameras were painted over in Sochaux, Belfort, Cateau-Cambresis, and Surmoulin
- Three radars burned in Lot-et-Garonne, making 46 of 49 disabled there; one burned in Saint-Herblain to join the ⅔s rendered inoperable in Loire-Atlantique; and two more burned in Mesnil-le-Roi and Mureaux, another two in Couvrot, four in Puy-en-Velay, two in Haute-Garonne, one on Bordes, one in Hérault, another in Matelles, one in Loudes, and three in Gers
- A radar at Truttemer-le-Grand, one on the Mazures coast and another in town, one at Pinas, one in Ouilly-le-Vicomte, one in Fourdrain, two in Tarn, one in Landivisiau, one in Monbalen, two in la Vienne, and another in Chavagne were torched
- A radar was sawed from its post then taken away and burned in Villerbon
- One was wrapped up securely in Goult
- Five radars burned in Ariège, and three of those were completely destroyed
- Six days after it was first installed, a radar in Saint-Laurent-des-Arbres was destroyed
- A nicely-wrapped gift box covered a camera in Domalain
- A mobile radar station posted on the D-928 was taken out of service for the tenth time, and another was victimized at Thillot
- “Not a week goes by without a machine taken out of service” reports Le Bien Public of the Côte-d’Or
There’s a strange feature of Obamacare. If your income is low, the government subsidizes your health insurance premium. But if your income is higher than you thought it would be, you’re supposed to pay some of that subsidy back when you file your taxes. But there’s a limit to how much you have to pay back. Because of this, the government is paying out about a billion dollars in subsidies that people don’t qualify for and yet will never have to repay.
Ministers in Samoa are defying the government’s attempt to tax them on the offerings they accept in church.

I have, to my surprise, suddenly retired.

This has various ramifications, mostly pleasant ones, but among which is that I need to retool my tax resistance strategy. That strategy has until now involved avoiding or resisting taxation on earned income by means of things like tax-deferred retirement contributions. Now I have to prepare for a future without any earned income to speak of, in which I will instead be drawing down those tax-deferred accounts.

This is my first draft of a game plan for the coming years. There are a lot of moving parts and a lot of uncertainty, and so it’s been challenging to draw this up.

I decided not to adjust numbers for inflation. I figure that allowable HSA deductions, standard deductions, Social Security, etc. will more or less track inflation and so it will be a wash as far as my calculations are concerned. I also assume a 3% real rate of return on invested money, which I understand is considered to be on the conservative end of what is likely (but who knows?).

The further my plans go into the future the more unreliable they are because of all of the unknowns (what will the market do? what will Congress do about Social Security? will artificial intelligence turn us all into paperclips?). For want of a way to meaningfully plan for possible scenarios like the collapse of the U.S. government, the global dominance of artificial superintelligence, and so forth, my scenarios instead assume that the future will be more or less a later-to-arrive version of the present, in which I am older but playing essentially the same game by the same rules. I’m posting this here today in part so I can look back at it and laugh later.

The biggest unknown, or one that looms large in my mind anyway, is how long I’ll be around to enjoy retirement. One can’t count on even one more day, but one ought to plan ahead anyway. The typical life expectancy for someone my age is something like 81. But my parents are both alive and on the cusp of 90 and three of my four grandparents made it into their 90s too, so I think I should be prepared for the possibility that I may stick around longer.

My goal is to have a comfortable and secure retirement (and hopefully a long and healthy one) and to continue to successfully resist funding the U.S. government. Can I do that if I retire today?

Just about every year since I started resisting, I’ve put aside 40–50% of my income into tax-deferred retirement accounts and a health savings account (HSA). In years when my income was lower than it needed to be to avoid the federal income tax, I’ve transferred some of the tax-deferred money into a Roth IRA, taking that amount as current-year income while staying within the 0% tax bracket. A couple of years back I stopped using the HSA to pay for health expenses and started using it as another retirement savings vehicle.

Early Retirement: Ages 57½–59½

So I start with a pretty good hunk of change in retirement accounts. However, I’m only 57½. I cannot begin to tap these accounts without penalty until I turn 59½, with a couple of exceptions:

I can withdraw from my HSA to pay for past health expenses I had paid for out-of-pocket (yes, I saved the receipts), and for current health expenses.
I can withdraw from my Roth IRA any principal I added at least five years ago (but not any gains, or anything I added more recently).

So for the next two years, before I turn 59½, I need to live off of my current cash savings (~$24k) + about $2k from my HSA + about $38k from my Roth = $64k. Can I do that?

My current spending runs to about $27k per year in rent, food, etc. (not counting health expenses for which I could tap the HSA). $64k gives me twice that and then some, so that feels safe to last two years.

I have brought in only about $15k in earned income this year. But I was making HSA and IRA deposits as though I were going to earn a standard year’s income. As a result I have way more deductions than I need to shield that much income from income tax. This gives me the opportunity to generate more tax-free income by doing another Roth transfer this year, probably to the tune of $43k or so. That will help later on.

Pre-Medicare: Ages 59½–65

When I turn 59½ I can start drawing down both my tax-deferred and Roth IRAs as much or as little as I’d like. (Starting at age 75, required minimum distributions may change this calculus a bit; I’ll get to that later.)

If I pull no more than $22k from my tax-deferred IRA per year, and deposit the maximum (currently $5,400) in my HSA, this will result in an adjusted gross income less than the standard deduction, resulting in no taxable income. (This also ensures that I remain eligible for Covered California’s high-deductible health insurance plan, so I can make HSA deposits.) Because none of this income is considered earned income in the current tax year; there is also zero self-employment / social security tax. If I supplement that ~$16k spending money with another $21k from my Roth IRA, that gives about $37k in spending money.

For the next several years I hope that the IRS will continue to drop the ball on my past tax debt, letting it fall off the statute of limitations cliff year after year as they have for several years now. When they do this, I typically celebrate by making a charitable donation equal to the amount of the successfully resisted taxes. I hope to keep doing this, but this means subtracting $4–$6k from that $37k of spending money. But that still leaves me comfortably above my $27k budget, so I think I’m okay here.

Medicare Kicks In: Ages 65–69

When I have to join Medicare at age 65, I lose my high-deductible health insurance plan and can no longer contribute to my HSA. Medicare also has substantially more expensive premiums than my current plan. As a result, my healthcare expenses rise, and an important tax deduction vanishes.

This will be a good time to start tapping my HSA to pay for these extra expenses.

On the up side, my standard deduction increases to the You’re Officially Old level.

In 2037, if things go well, the last of my tax debts will be eliminated by the statute of limitations. I’ll make my usual charitable donation and will have no remaining federal tax debt.

Things are a little iffy toward the end of this 65–69 range: it’ll be touch-and-go depending on the market and on how frugal I’ve been in the previous years, but I may exhaust my Roth toward the end of this period. If so, I have options. I might tap the HSA to reimburse for past medical expenses (if I still have any stored up), or I might have to take more out of my tax-deferred IRA, which could put me into taxable income territory. Another option would be to apply for Social Security earlier than I otherwise planned to.

What if the IRS Seizes that Tax Debt?

The IRS has failed, for many years running, to collect taxes they say I owe them. But this isn’t because I have some great ninja asset-hiding scheme. I haven’t buried my IRA in a hole in a tax haven or anything like that. I’ve just been overlooked by a dysfunctional bureaucracy. That could change at any time.

The total amount I owe at this point is a little under $90k. If the IRS seizes money from some account of mine, that may have additional tax implications. If they seize it from a tax-deferred retirement account or from my HSA, the amount they seize would count as potentially-taxable income in the year it was seized. (I think early-withdrawal penalties are waived in such a circumstance, but if not, that too might be an issue if this happens before I turn 59½.) If they seize it from my bank account or from my Roth, that leaves less in those accounts for me to use to offset potentially-taxable income.

In short, such a seizure could throw a wrench in my plans, and I’d have to rejigger things.

Because it’s difficult to predict if, when, or in what manner this might happen, I haven’t tried to account for this in my scenarios. But it’s a Sword of Damocles that dangles over these plans and could disrupt them a bit.

One thing I’m unsure about is whether the act of beginning to draw down my retirement accounts will make those accounts more salient to IRS enforcers. I think they tend to be reluctant to seize money from retirement accounts; but this may be more the case when those accounts represent retirement savings than when they represent retirement income. It’s possible that beginning to take IRA withdrawals may trigger a levy.

Of the ~$90k in tax debt, about a third of it is interest and penalties added by the IRS to the amount I originally did not pay. If seized from me, I could apply to the War Tax Resisters Penalty Fund for reimbursement of these penalty-and-interest amounts. The fund has a good record of reimbursing requests like these, but it has not seen many requests in recent years, and a request for ~$30k would be an especially large one, so it is uncertain how much reimbursement I could expect from such an application. I am not sure whether such a reimbursement would officially be considered taxable income or more along the lines of a gift.

Social Security Kicks In: Ages 70–74

When I hit age 70, I must begin taking Social Security (I could start earlier, but I think it is to my advantage to wait). In current dollars, my expected benefit is about $35k/year. (The Social Security trust fund is expected to give out by then, which could mean a reduction in benefits if Congress has the guts to try that. This would change some of the numbers that follow, but not the basic strategy.) Social Security benefits are taxable, but only according to a strange formula:

If your “combined income” is < $25k, they aren’t taxed at all.
If your “combined income” is between $25k and $34k, half of your Social Security benefits become part of your adjusted gross income.
If your “combined income” is > $34k, 85% of your Social Security benefits become part of your adjusted gross income.

So my best bet for avoiding federal income tax entirely is to keep my “combined income” below $25k. What is “combined income” you ask? It seems to be whatever would be my adjusted gross income anyway (at this point: what I pull from my tax-deferred IRA, plus any Roth conversions) plus half of my Social Security benefits.

Naïvely, if I were to continue to withdraw about $20k/year from my IRA, my “combined income” would be about $38k, which is too much. So what can I do about that?

There’s a trick called “qualified charitable distributions” that allows retirees after age 70 to transfer money directly from their tax-deferred retirement accounts to certain types of charities; when they do so the amount of the transfer does not count as income. So if I get $35k in Social Security, withdraw $7k from my IRA to supplement that, and donate $13k to charity from my IRA, the numbers look something like this:

Spending money: $35k + $7k = $42k
Combined income: $35k÷2 + $7k = $24.5k
Adjusted gross income: $7k

So I remain tax-free despite the new income source, and indeed my spending money budget can go up. If I stay frugal, I can even use some of this extra money to rebuild my Roth by means of Roth conversions. That may come in handy later on when my HSA runs out (around age 77 according to my projections).

Social Security can be seized by the IRS to satisfy tax debt. (Typically only 15% of your check can be seized, but more can if The Man decides to make a big deal about it.) However if things go well I won’t have any remaining tax debt by the time I turn 70, so this won’t be an issue.

You may wonder why I plan to withdraw anything at all from my IRA at this point, since the Social Security benefit by itself wouldn’t be taxable and yet would be enough for me to live on comfortably. The answer is that I have to withdraw some of that money eventually — see below — and so there’s no real disadvantage to doing so at this stage if there’s plenty to be had. If I don’t have any spending needs to justify the withdrawals, I can take them in the form of Roth conversions and charitable contributions. If the market tanks, I can leave my IRA alone and coast on Social Security for a while.

Required Minimum Distributions: Ages 75+

At age 75, another rule kicks in: I must take a certain amount from my tax-deferred IRA every year whether I want to or not (up to now, whether and how much to withdraw has been entirely up to me). The amount I have to withdraw is based on the amount in the account and my age. Under the projections I’m working with, this will have the effect of slightly increasing the amount I withdraw from my IRA.

But because of the “qualified charitable distributions” trick described above, I can simply increase my charitable giving to match and thereby continue to keep my combined income and adjusted gross income numbers below their respective lines.

I’ve run the numbers through 2068 at which time, if I am still alive and kicking, I will celebrate my 100^th birthday. Should I be so lucky, according to my best-guess estimates, I will have spent about $2.3 million in today’s money on my own modest upkeep during retirement, will have given about $600k to charity, and will still have a little gas in the IRA tank in case they’ve invented a miracle longevity pill or I want to leave a bequest somewhere or other. When I look at it that way, I feel astonishingly wealthy and fortunate (though fortune may have its own ideas for my future). Yet, when I describe my frugal retirement strategy to others I not infrequently am met with a response that suggests I’m consigning myself to sad poverty or something like that.

What if I have unusual expenses I haven’t anticipated here, e.g. I need long-term care or I want to take a bucket list vacation somewhere fancy or I want to replace my failing body with the latest consumer model robot parts? Well, I do have a considerable extra room in my potential budget if I’m willing to step over the taxable income line. If in some year I need to spend thousands of dollars on some emergency (or splurge) expense, I can withdraw a little extra from the IRA or I can neglect to make a charitable donation that year. This makes me vulnerable to income tax, but I can always just neglect to pay the tax and try my luck against the IRS enforcement bureaucracy, which has been a good bet thusfar.

Of course, nothing will turn out exactly like I’ve planned. Trying to project things 40 years into the future based on the current financial economy and political economy and my current lifestyle needs is nuts. But as a back-of-the-envelope calculation to help me figure out whether now is a good time to attempt to slip into a secure retirement and continue to resist, it’s been a good exercise and has given me the confidence to go ahead. It’s also helped me to plot out some strategies I can use along the way (if I stay alert for changes and remain flexible) to make things go easier.

ages	0-tax target	strategy
57½–59½	AGI < $16,100	Limited Liquidity: Spend down cash, use Roth principal to supplement. Continue maximum deposit to HSA. Do Roth conversions to fill out your 0% bracket. Pay medical expenses without dipping into the HSA. Continue ~$5k/year charitable contributions. Your post-medical spending budget is ~$30k/year.
59½–65	AGI < $16,100	IRAs available: Tap tax-deferred IRA to the extent you can while remaining in the 0% bracket (~$22k). Otherwise pull from the Roth. Only do Roth transfers if you have extra room in your 0% bracket. Continue maximum deposit to HSA. Pay medical expenses without dipping into the HSA. Continue ~$5k/year charitable contributions. Your post-medical spending budget is ~$30k/year.
65–69	AGI < $19,050	Medicare: You must join Medicare, so you lose the health insurance plan that allows HSA contributions. Your standard deduction rises, so you can pull more (~$25k) from your IRA. Pull whatever else you need from the Roth. Medical expenses likely to rise (Medicare premiums and deductibles); budget about $6.5k for this, but pay from your HSA. Continue to make charitable donations until the last tax debt vanishes in 2037. Your post-medical spending budget is ~$30k/year.
70–74	CI < $25,000	Social Security: Your Roth may be depleted; you may have to rely on your tax-deferred IRA. You begin taking Social Security, about $35k per year. Make “qualified charitable donations” directly from your tax-deferred IRA to keep your combined income low. Make more Roth conversions if you can, as this will come in handy when your HSA gives out. Your post-medical spending budget is ~$40k/year.
75+	CI < $25,000	Required Minimum Distributions: Your Roth may be depleted, and your HSA is emptying as well. This makes it a little more difficult to stay in the zero-tax zone, but still manageable. Increase your qualified charitable donations to make up for additional IRA withdrawals. Your post-medical spending budget is ~$35–40k/year.

After doing some more research I’ve found a few snags and caveats in the first-draft tax-free retirement plan I posted earlier this month. These are the most concerning ones:

I planned that in a couple of years, I would drop my adjusted gross income considerably for a few years because I will have fewer tax credits I can play off against taxable income to get my tax rate down to zero. This is fine from a spending point of view, because I will be able to tap some additional income that does not appear in AGI. However, this threatens to push me out of the Covered California subsidized health insurance marketplace and onto its health-insurance-for-poor-people plan (Medi-Cal). If that were to happen, I would lose my high-deductible health insurance plan and would no longer be able to contribute to a health savings account. That would eliminate a nice tax deduction and also a good tax-free way of paying for health expenses later on in retirement, so I would like to avoid that if possible.
Apparently you cannot use any portion of your required minimum distribution from an IRA to make Roth conversions. I hadn’t accounted for that in my original plan.
The “combined income” factor that determines how much of my social security benefit becomes part of my adjusted gross income, and so potentially my taxable income, does not adjust for inflation under current law. Currently, if my CI is below $25k, none of my social security is taxable; if it is higher than that but below $34k, 85% is taxable; if it is higher than that, 100% is taxable. But those thresholds are set in stone by current law; if nothing changes, they will be the same in 2037 when I turn 70. In order to keep my CI that low, my spending budget has to stay low to match, but money won’t go as far then, so that represents a significant hit.
Oh yeah, about that social security: Currently, the social security program is scheduled to start running short of money in 2032, before I plan to start taking benefits. If nothing is done to fix this problem, benefits could drop to about three quarters of their currently-anticipated values.

Here are some thoughts on how I might address these conundrums:

(Low AGI=no HSA) There are a few options here:
- I could just take the hit and go on Medi-Cal. The loss of the deduction would mean I would withdraw less from my IRA during the years when I had intended to fund the HSA. Having less money in the HSA would mean I would have to pay for medical expenses from IRA withdrawals or from social security in my early 70s instead. Neither of those things breaks my plan, but it makes my zero-tax budgets slightly tighter.
- I could let my AGI climb out of the zero-tax zone and take the federal tax hit. After all, I’ve been owing (and neglecting to pay) self-employment tax for years. If I were to owe and not pay a smaller amount of income tax, that would for practical purposes amount to the same policy I’ve long been operating under.
- I could withdraw enough money from my IRA to raise my AGI sufficiently, but then spend that extra money on courses at the university up the street. That way I could qualify for the federal “Lifetime Learning Credit” with which I could eliminate any tax due on the higher income. That university has a good set of courses on artificial intelligence in its computer science department, and on the ethics of technology in its philosophy department, which both seem like good bets for positioning myself to be more capable to contribute meaningfully to humanity’s attempts to weather the incoming crisis. This currently seems like the most attractive option.
(RMDs and Roth conversions) My options here appear to be two:
- Stop making Roth conversions when I hit age 75 and have to start taking RMDs. Turns out that’s no big deal and doesn’t really change my plan much at all.
- Take additional IRA withdrawals over and above the RMDs in order to make Roth conversions. I don’t think this is worth doing.
(CI not indexed for inflation) I don’t have a plan for how to deal with this. The ramifications do not begin until 2038, which is far enough out that I assume the law will change in some meaningful way by then, whether for the worse or the better, and I’m better off waiting to cross that bridge when I come to it.
(Social Security unsustainable) If this happens, this will result in slimmer budgets for me during my social security years (after age 70), but nothing unendurable. However, as with the previous item, I assume that by then the law will have changed in some way. The politicians in Congress aren’t about to let every voter on social security take an abrupt 20% cut without trying to cook the books in some manner. Someone will have to get screwed to prevent that from happening, and I might very well be one of the someones, but it probably won’t be in the manner this scenario suggests.

OK. I’m getting pretty tired of running all these numbers, but I wanted to be extra careful to get things right. With much of the above (and several other smaller tweaks) incorporated into my game-plan, here’s how it’s shaking out now:

ages	0-tax target	strategy
57½–59½	AGI < $17,100	Limited Liquidity: Spend down cash, use mature Roth principal to supplement. Continue maximum deposit to HSA. Do Roth conversions to fill out your 0% bracket. Pay medical expenses without dipping into the HSA. Continue ~$5k/year charitable contributions. Your post-medical spending budget is ~$30–35/year.
59½–65	AGI ~$23,000	IRAs available: Tap tax-deferred IRA to get to the minimum AGI necessary to keep your health plan (~$29–$30k/year). Beyond that, pull from the Roth (~$18k/year). Continue maximum deposit to HSA. Pay medical expenses without dipping into the HSA. Continue ~$5k/year charitable contributions. Your post-medical spending budget is ~$35–36k/year but you’ll need to spend $4–5k of that on university courses to qualify for the Lifetime Learning Credit to bring your federal income tax down to zero.
65–69	AGI < $20,050	Medicare: You must join Medicare, so you lose the health insurance plan that allows HSA contributions. Pull annually about $21k from your traditional IRA, and $18–19k from your Roth. Medical expenses are likely to rise (Medicare premiums and deductibles); budget about $6.5k for this, but pay from your HSA. Continue to make charitable donations until the last tax debt vanishes in 2037. Your post-medical spending budget is ~$33–35k/year.
70–74	CI < $25,000	Social Security: You begin taking Social Security, about $35k per year (Congress willing). Withdraw about $17k per year from your IRA, but donate the bulk of that ($15k) via “qualified charitable donations” to keep your combined income below the (hopefully similar to today) 0% threshold. In addition, do $5k/year in Roth conversions, as this will come in handy when your HSA gives out. Your post-medical spending budget is ~$37k/year.
75+	CI < $25,000	Required Minimum Distributions: The required minimum distributions do not change the pace of your traditional IRA withdrawals very much, putting them in the $18k–25k per year range. In addition, you can take $1–2k per year from your Roth; more if you have reason to expect your dreams/nightmares of living into your 90s will be thwarted. Your HSA is depleted or soon will be, so you’ll be paying for medical expenses out of your IRA withdrawals instead. Stop doing Roth conversions. Keep up your qualified charitable donations of $12k–$18k per year to keep your combined income sufficiently low. Your post-medical spending budget is ~$36–38k/year.