Questions on Roth conversions and when to spend

deserat

Thinks s/he gets paid by the post
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I have been writing REWahoo about my situation and he suggested I post here. I had gone to several financial managers seeing if I should have them manage my portfolio or 'roll-my-own.' He convinced me to do it myself and I now have a spreadsheet for my IRA to Roth conversion plan as well as projected income streams.

I am semi-ER and am in a gap situation (6 years) before I receive a nice pension. I have played around with ORP and with several scenarios (I use age 100 as the end). Bottom line, I will see a significant increase in my yearly spend rate ability if I convert my IRAs to Roths. In ORP they show a 'bite the bullet' approach with transitioning the IRA to Roth in two years before I receive the pension with a large tax consequence of course. They then show the spending done out of the Roth at the end of my life.

So, my questions - in the ORP model they show me spending my Roth at the end of my life and not earlier. Do you know the reason for that? I can't find a good consistent reason in my research. My next question, I am planning on smoothing out the IRA to ROth conversion over the six years and maybe a bit more into my pension stage - does that make sense?

Lastly, has anyone come up with a good AA? I am sort of in Nords situation where with the upcoming pension being a big bond, so I could be a lot more risky in my portfolio. I currently use the offered 'lifestrategy-like' funds with later end dates (2040 or so).

Thanks in advance for your ideas...BTW, I am a long time user of this board, just was gone for awhile. I helped Nords write his book a long time ago on the Reservist chapter.
 
Deserat. I am going the same route as you.

I am also considering a big IRA->Roth conversion. I put together a draft spreadsheet. Comparing conversion to non-conversion showed a slight advantage to conversion (especially for heirs). Of course, if my assumptions are off none of that matters.

I am 4 years from Medicare and DH already has Medicare. The big expense that is driving my decision is the high-income Medicare premium. I think it would be best to bite the bullet now. If I convert to the higher% tax now, I think it could save future tax pain.

Once DH takes SS and we are both on medicare and RMDs kick in, we won't have any options. We have pensions and rentals, along with investment income.

I didn't feel that iorp considered the Medicare premium for high incomes.

Any critiques on my plan are welcome.
 
I am 4 years from Medicare and DH already has Medicare. The big expense that is driving my decision is the high-income Medicare premium. I think it would be best to bite the bullet now. If I convert to the higher% tax now, I think it could save future tax pain.

Once DH takes SS and we are both on medicare and RMDs kick in, we won't have any options. We have pensions and rentals, along with investment income.

I didn't feel that iorp considered the Medicare premium for high incomes.

Any critiques on my plan are welcome.

You've highlighted some areas I have been ignoring - I am cynical about SS, and yet, if I include it, it adds even more pension income. I am frankly aghast at even the low number of amount of spending after taxes that ORP shows (no IRA to Roth conversion). Even in this gap situation, it shows I can spend much more than I do now.

I am not yet comfortable with trusting that. The earning and saving habit is severely ingrained.

I will have TRICARE as my insurance - although your point about Medicare and the premium for higher incomes is spot on. I tend to think the SS will also have a premium if anyone has some other means.

And RMDs - that's why I want to get the Roth conversion done before I am 70.

We shall see - prepare for the worst and hope for the best or somewhere in between :)
 
I am also trying to finish converting my tIRA to Roth by 70.

If I see I'm going to pass on some assets, which is likely, I will spend Roth before highly appreciated assets in taxable, since my heirs will get a new basis for those stocks. But I will sell stocks that have little or no gain before spending from the Roth.

If I had to, I would even break into my Roth now if it kept me in a favorable tax position, namely to keep the ACA subsidy. So far that hasn't been needed.
 
We shall see - prepare for the worst and hope for the best or somewhere in between :)

I plan to convert half of my 2018 IRA->Roth now and the remainder for 2018 in December. I am splitting it because the tax bite is big and if something changes I have the hedge. I also will have time to tweek the conversion to the 2018 tax scenario.
 
My long-term plan shows us being in the 22% tax bracket once SS and RMDs start.... I don't see much advantage on converting at 22% now... but I may consider it for a couple years once we are no longer paying state income taxes.

RMDs don't scare me... pay 22% later vs 22% now.
 
I have been writing REWahoo about my situation and he suggested I post here. I had gone to several financial managers seeing if I should have them manage my portfolio or 'roll-my-own.' He convinced me to do it myself and I now have a spreadsheet for my IRA to Roth conversion plan as well as projected income streams.



I am semi-ER and am in a gap situation (6 years) before I receive a nice pension. I have played around with ORP and with several scenarios (I use age 100 as the end). Bottom line, I will see a significant increase in my yearly spend rate ability if I convert my IRAs to Roths. In ORP they show a 'bite the bullet' approach with transitioning the IRA to Roth in two years before I receive the pension with a large tax consequence of course. They then show the spending done out of the Roth at the end of my life.



So, my questions - in the ORP model they show me spending my Roth at the end of my life and not earlier. Do you know the reason for that? I can't find a good consistent reason in my research. My next question, I am planning on smoothing out the IRA to ROth conversion over the six years and maybe a bit more into my pension stage - does that make sense?



Lastly, has anyone come up with a good AA? I am sort of in Nords situation where with the upcoming pension being a big bond, so I could be a lot more risky in my portfolio. I currently use the offered 'lifestrategy-like' funds with later end dates (2040 or so).



Thanks in advance for your ideas...BTW, I am a long time user of this board, just was gone for awhile. I helped Nords write his book a long time ago on the Reservist chapter.



Our CPA said usually Roth dollars are the last to be spent, because people leave money in Roths since the growth is tax-free. Therefore many times Roths end up mainly benefitting the heirs.
 
My long-term plan shows us being in the 22% tax bracket once SS and RMDs start.... I don't see much advantage on converting at 22% now... but I may consider it for a couple years once we are no longer paying state income taxes.

RMDs don't scare me... pay 22% later vs 22% now.



This is why we aren’t doing conversions. We may have a year or two when we could do very small conversions but it hardly seems worth it to convert 0.3% of our net worth to a Roth.
 
Our CPA said usually Roth dollars are the last to be spent, because people leave money in Roths since the growth is tax-free. Therefore many times Roths end up mainly benefitting the heirs.

Agreed. Main benefit is inheritance. The alternative is to face the RMD if you live that long and pay the taxman, in return you get to blow the dough...as opposed to watching the dough rise.
 
Let's say you have $2M left: $1M in taxable, with $500K basis, and $1M in Roth. Say you will only spend $1M.

If you spend from taxable, and your cap gains are taxed at 15% (because of SS and pension benefits, perhaps), you will pay $75K in fed taxes on that $500K LTCG. Possibly more in state taxes. So you must pull an additional $75K out of your Roth. Your heir gets $925K in an inherited Roth. Gains on this account for your heir will be tax free, but MRDs are required and it will eventually wind up in taxable, where gains will be taxed.

If you spend from the Roth, the Roth is gone, but you don't have to dip into taxable. Your heir gets $1M in a taxable account, with $1M in basis. Future gains will be taxed.

I'm not really sure which is better to inherit. I suppose the heir could probably make more that $75K in tax free investment gains in the Roth to make up the difference, before the Roth gets converted? I thought I was making a case for using the Roth first, but maybe I'm wrong, and it's better to leave the Roth for last, even over highly appreciated taxable holdings?
 
My long-term plan shows us being in the 22% tax bracket once SS and RMDs start.... I don't see much advantage on converting at 22% now... but I may consider it for a couple years once we are no longer paying state income taxes.

RMDs don't scare me... pay 22% later vs 22% now.

According to the current tax scheme, later might be 28%. The 22% tax cuts are only until 2025, then 28% comes back.

The choice is pay 22% now or pay 28% later. Add the increased medicare for two in the future and the risk of conversion now is worth it.

Once two becomes one, the tax bracket will be even higher.
 
I am in that situation where Roth conversions are basically break-even on paper based upon today's tax laws.

However, the future is uncertain and I figure it's good to have options. So, I converted some tIRA money to Roth IRA's just in case I have some years where going over a certain amount of income may be a big problem.
 
The key is for most that are married, the saving Roth for last can be huge when there is only one. Loss of a spouse can be bad enough. But getting to pay double in taxes for it is adding insult to injury. If you are always single, not a consideration really.
 
According to the current tax scheme, later might be 28%. The 22% tax cuts are only until 2025, then 28% comes back.

The choice is pay 22% now or pay 28% later. Add the increased medicare for two in the future and the risk of conversion now is worth it.

Once two becomes one, the tax bracket will be even higher.

I think that it is more likely than not that Congress will act to make the 22% permanent before it increases to 25%.... but I understand your point and you are entitled to your opinion.

I may consider converting to the top of the 22% tax bracket if we redomesticate to Florida in 2020 and my current 6.8% state income tax goes away... but I'm not keen on paying 28.8% combined now (22% federal and 6.8% state) vs 22% combined later (or even 25% if you are right in the reversion of the federal tax rate).

And I concede the higher effective tax rate if single vs MFJ but DW and I are both in good health so I'll take my chances on that.
 
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The key is for most that are married, the saving Roth for last can be huge when there is only one. Loss of a spouse can be bad enough. But getting to pay double in taxes for it is adding insult to injury. If you are always single, not a consideration really.

I don't get the "saving Roth for last" part.... can you elaborate?
 
According to the current tax scheme, later might be 28%. The 22% tax cuts are only until 2025, then 28% comes back.

The choice is pay 22% now or pay 28% later. Add the increased medicare for two in the future and the risk of conversion now is worth it.

Once two becomes one, the tax bracket will be even higher.

I think that it is more likely than not that Congress will act to make the 22% permanent before it increases to 28%.... but I understand your point and you are entitled to your opinion.
I think the 22% tax bracket becomes 25% if tax brackets revert.
The 24% tax bracket becomes 28%.
 
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I don't get the "saving Roth for last" part.... can you elaborate?

In that context, I was referring to Roth vs tIRA. When one dies before the other, which is almost always the case, the single left behind now would pay single rate higher taxes on withdrawals from tIRA, vs tax free from Roth.
 
Also note you might have lost your 0% window for CGs with the new single status. So for marrieds, that could be a good reason to pull from taxable before Roth.
 
I think of ROTHs as being more flexible than other savings - thus using them last may make some sense. I'm no expert, but my understanding is that passing assets to the next generation with ROTHs has real advantages in many cases.

There are no taxes involved in withdrawing from ROTHs (flexible, therefore, because one can "titrate" their taxes by withdrawing some funds from taxable and some from ROTHs to avoid exceeding tax brackets.)

I believe one can avoid the Medicare cost trap by the same method.

Also, there are no RMDs for the principal owner of the ROTH. All in all, it seems like you would keep the "best" for last, but YMMV.
 
I am semi-ER and am in a gap situation (6 years) before I receive a nice pension. I have played around with ORP and with several scenarios (I use age 100 as the end). Bottom line, I will see a significant increase in my yearly spend rate ability if I convert my IRAs to Roths. In ORP they show a 'bite the bullet' approach with transitioning the IRA to Roth in two years before I receive the pension with a large tax consequence of course. They then show the spending done out of the Roth at the end of my life.
I’m surprised by how quickly the room for a Roth IRA conversion disappears after a pension starts. We’re hustling to finish ours before my spouse’s Reserve pension starts, even if the savings appear to be tax-neutral.

So, my questions - in the ORP model they show me spending my Roth at the end of my life and not earlier. Do you know the reason for that?
Our CPA said usually Roth dollars are the last to be spent, because people leave money in Roths since the growth is tax-free. Therefore many times Roths end up mainly benefitting the heirs.
I also think it’s about the inheritance. Normally a surviving spouse would take over the Roth and not pay any taxes on the inherited distributions.

I don’t understand Roth IRAs well enough to know what happens if the surviving spouse doesn’t spend the money (or doesn’t inherit the Roth IRA). Are Roth IRA distributions taxable when an adult child inherits? Are they taxable when some other person inherits? Are they taxable when a minor child inherits, or could they be put into a 529 or UGMA?

Another reason for ORP’s behavior could be “saving” the Roth distribution to (1) let the account compound without additional taxes and (2) for any late-in-life expenses like long-term care. If you needed to spend an additional $100K/year then you could withdraw it from the Roth with no tax implications. If you had to spend that additional $100K/year from long-term capital gains then it’d be taxed.

Even worse, raising your spending could raise your AGI and trigger the higher Medicare premium IRMAA “tax”.
https://www.kitces.com/blog/irmaa-m...-premium-surcharges-new-2018-magi-thresholds/

When I became my father’s conservator and simply rebalanced his assets, the boost to his AGI also triggered IRMAA:
https://the-military-guide.com/how-i-cost-my-dad-over-2000-in-medicare-benefits/

IMy next question, I am planning on smoothing out the IRA to Roth conversion over the six years and maybe a bit more into my pension stage - does that make sense?
You’d want to get it done in your lowest income-tax brackets, and you’ll certainly raise your income when you start taking your pension. It makes more sense to spread the conversions out over six years (and finish the year before your pension starts?) instead of just two years. We’ve been converting traditional TSPs and traditional IRAs into Roth IRAs since 2002, and we’ll finish the last increment this year.

Lastly, has anyone come up with a good AA? I am sort of in Nords situation where with the upcoming pension being a big bond, so I could be a lot more risky in my portfolio. I currently use the offered 'lifestrategy-like' funds with later end dates (2040 or so).
Mathematically you could go >90% equities with your other assets, especially because the (imperfect) analogy for an inflation-adjusted federal pension is the income from a portfolio of 30-year TIPS or I bonds.

Considering the emotions of behavioral financial psychology, the volatility of a high-equity portfolio can be impressive. You’d feel bad if a recession hit the year after you went from a L2040 fund to a S&P500 index or total stock market index and whacked the balance by 25%. It’d recover in another 5-10 years, but you’d still feel bad about it.

A compromise would be moving to the equivalent of an L2050 fund or (if they’re offered) an L2060 fund.

A third (more difficult) option would be going to >90% equities and trying to learn to ignore volatility in the portfolio, especially if you end up living from pension & Social Security (and an occasional Roth IRA withdrawal).

I helped Nords write his book a long time ago on the Reservist chapter.
You sure did, and thank you again! The posts on the Reserve pension system (and on calculating a Reserve pension) are still the site’s heaviest traffic. It’s been that way every month for over five years.

Even in this gap situation, it shows I can spend much more than I do now.
I am not yet comfortable with trusting that. The earning and saving habit is severely ingrained.
It’s hard to change the frugal habits that got you to FI, no matter what the math says. I’m still going through that emotional adjustment process myself.

I’ll point out that 16 years of cost-of-living adjustments (the same COLA as the Social Security CPI COLA) have raised my military pension by nearly 40%. That 40% includes three years of zero COLA.

I’d rather live in a world where I have a small COLA (low inflation) than a big COLA (1970s-1980s), yet even a bunch of small COLAs add up.

To raise your income even higher, would you be receiving any untaxed VA disability compensation with that? If your VA disability rating is <50% then the disability compensation offsets your pension, but it still dramatically lowers your federal income taxes.

If your VA disability rating is 50% or higher, then your disability compensation no longer offsets your military pension but instead becomes Concurrent Retirement and Disability Pay, so it’d be added to your pension.
https://themilitarywallet.com/concurrent-receipt-military-retirement-pay/

CRDP is not a good thing (nobody wants a VA disability rating of at least 50%) but if you start at a 30% VA disability rating and your joints get steadily worse (osteoarthritis) then you’d hit 50% and CRDP in a regrettably short time. My tinnitus and bilateral knee ACL tears are already a total of a 30% VA disability rating, and osteoarthritis can steadily reduce the joint’s flexibility (and mobility) to raise the disability rating. I’m also inexorably approaching a 10% disability rating for hearing loss, which is pretty common among vets who’ve been around engine noise (even with hearing protection).

Or if Congress eliminates the offset between military pensions and VA disability compensation, then your income would rise by a few hundred dollars per month.

Apparently researchers think that the spending reluctance of frugality is so common (and so severe) among women retirees that they’ve named it “Bag Lady Syndrome”. Maybe this is just media hype, but a search for that phrase returns over 10M results.

I will have TRICARE as my insurance - although your point about Medicare and the premium for higher incomes is spot on.
Yep, and that means your health-insurance premiums will drop for a few years until Medicare (with bigger premiums) & Tricare For Life (with no premiums) kick in at age 65. So your initial spending might actually drop when your pension starts and then at age 65 you could offset your Medicare premiums with Social Security distributions. (Or delay SS to age 70.) The net effect is that you still end up with more annual income.

Good “problems” to have. You’re not looking at yachts and private jets, but you’re absolutely able to enjoy cruises and travel-hacking first-class airfare. The key is getting comfortable with the spending (and the volatility).

Let's say you have $2M left: $1M in taxable, with $500K basis, and $1M in Roth. Say you will only spend $1M.

If you spend from taxable, and your cap gains are taxed at 15% (because of SS and pension benefits, perhaps), you will pay $75K in fed taxes on that $500K LTCG. Possibly more in state taxes. So you must pull an additional $75K out of your Roth. Your heir gets $925K in an inherited Roth. Gains on this account for your heir will be tax free, but MRDs are required and it will eventually wind up in taxable, where gains will be taxed.

If you spend from the Roth, the Roth is gone, but you don't have to dip into taxable. Your heir gets $1M in a taxable account, with $1M in basis. Future gains will be taxed.

I'm not really sure which is better to inherit. I suppose the heir could probably make more that $75K in tax free investment gains in the Roth to make up the difference, before the Roth gets converted? I thought I was making a case for using the Roth first, but maybe I'm wrong, and it's better to leave the Roth for last, even over highly appreciated taxable holdings?
I think that if a spouse won’t inherit a Roth IRA, this makes a good case for the Roth IRA owner to spend down the Roth IRA and let the taxable accounts be inherited with a basis step-up.

When I started managing my father’s assets, he was 77 years old, already a widower, and had already spent his IRA. His only remaining investment accounts were taxable ones. He and I never had a discussion about it, but I suspect that tax issue is why he spent his IRA before RMDs. When he died, his taxable assets passed with a humongous step-up in basis. He’d held some of those taxable shares for over 25 years.
 
I don’t understand Roth IRAs well enough to know what happens if the surviving spouse doesn’t spend the money (or doesn’t inherit the Roth IRA). Are Roth IRA distributions taxable when an adult child inherits? Are they taxable when some other person inherits? Are they taxable when a minor child inherits, or could they be put into a 529 or UGMA?

No, the distributions generally aren't taxable to the heirs/beneficiaries.

https://www.rothira.com/roth-ira-beneficiary-rules

About midway down the page from the above link:

"If you leave your Roth IRA to your spouse, he or she will receive it and can basically treat it as his or her own. Your spouse won’t be required to take distributions or have to pay taxes.

If you name one or more people other than your spouse as a beneficiary, they will need to withdraw a minimum amount each year. You will find worksheets for IRA distributions here. There are several methods for calculating how much they withdraw. The benefit of the Roth IRA, compared with the Traditional IRA, is that your beneficiaries do not pay income tax on the distributions as long as you held the account for more than five years.

Your beneficiaries can also control the amount of distributions and the time over which they take them, depending on how they do the calculations. Stretching out the IRA gives the funds decades of tax-free growth in a Roth IRA."
 
Doug,

Thank you so very much for your exhaustive reply - to be honest there were parts where I will need to do more research, however, I don't mind that. You have always been so generous with your knowledge and advice and I really like that about you and appreciate it especially when you help me.

I have actually run my numbers in ORP with several scenarios. I also used Vanguard's Financial Engines service (I get access free through a previous employers 403B - I kept some of my tax-deferred savings in their retirement area mainly due to the very low fees) and it came up with a very similar number for my 'yearly spending.' It is mind-boggling to me....I try to have a decent lifestyle on 20-25% of what is projected. I will probably be donating a bit of it to organizations I deem worthy. As for other pursuits, no, not yachts, but I could probably own a small private plane and indulge in my flying hobby, if I wanted to. And more travel while I can do it.

As for spending the ROTH last, a lot of what has been bandied about here now makes sense. I don't have a spouse or dependents, so that means I will probably have to pay someone to take care of me when I am older. I know those costs can be prohibitive after having just gone through that with my mother. Being able to withdraw it with minimal tax consequence is a good goal.

As for the bag lady, yes, I can see that tendency. Actually, I live quite well compared to most people in the world. However, I have done it by getting a good education in an area that is fairly well paid, living well below my means, investing my savings, and paying for my large lifestyle material assets with as little debt as possible. I have a huge fear of being a burden, so that fear has driven me to be as self-sufficient as possible.

Now, to ensure the grasshoppers don't take it all......
 
If your VA disability rating is 50% or higher, then your disability compensation no longer offsets your military pension but instead becomes Concurrent Retirement and Disability Pay, so it’d be added to your pension.
https://themilitarywallet.com/concurrent-receipt-military-retirement-pay/

CRDP is not a good thing (nobody wants a VA disability rating of at least 50%) but if you start at a 30% VA disability rating and your joints get steadily worse (osteoarthritis) then you’d hit 50% and CRDP in a regrettably short time. My tinnitus and bilateral knee ACL tears are already a total of a 30% VA disability rating, and osteoarthritis can steadily reduce the joint’s flexibility (and mobility) to raise the disability rating. I’m also inexorably approaching a 10% disability rating for hearing loss, which is pretty common among vets who’ve been around engine noise (even with hearing protection).

Or if Congress eliminates the offset between military pensions and VA disability compensation, then your income would rise by a few hundred dollars per month.

Doug, I was a Reservist so I don't think I am eligible for the VA rating - I have not done anything towards that. Most of my injuries occurred when I was not on status, so I don't know that I would have a case for a disability rating. However, I guess I could go visit my local Legion and find out...I've had issues getting the VA to even issue me a card, even though they spam me about everything else. I've heard through other grapevine contacts I have, they are very interested in the female vets and supporting them.

I know that you did your rating assessment way after your retirement started. I was going to see what I could do after I truly have my pension. However, if you advise otherwise, I'm all ears.


When I started managing my father’s assets, he was 77 years old, already a widower, and had already spent his IRA. His only remaining investment accounts were taxable ones. He and I never had a discussion about it, but I suspect that tax issue is why he spent his IRA before RMDs. When he died, his taxable assets passed with a humongous step-up in basis. He’d held some of those taxable shares for over 25 years.

I may have this issue as well when my father passes, although, it depends when his spouse goes (before, after or way after).

The difference between my parents is amazing with regard to their financial status. If my mom had stayed married to my dad, her tragic situation at the end of her life would probably not have been as dramatic nor required the financial support I gave her. The decision to divorce him and then the myriad of cascading decisions after that were reflected in her final days. I am *so* lucky to have decided early to retire early and therefore work to embody the live below your means lifestyle.
 
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