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Old 05-10-2016, 12:21 PM   #21
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1) Harvest gains today and guarantee that I'll never pay taxes on those gains ever. Offsetting that benefit are larger traditional IRA balances on which I may, or may not, pay more in taxes in the distant future than I would if I had converted to a Roth.

2) Do a Roth conversion where I may or may not pay less in taxes over my lifetime in exchange for maintaining larger unrealized capital gains balances that are subject to tax.

In one case I guarantee tax free income forever. In the other case I pay more in taxes today in an attempt to gamble and win on future tax rules.
How do you account for the the differences in tax treatment of the future gains?

1) The gains are tax free now, but all future gains from it are taxable

2) Converted values and their future gains remain tax free "forever"

Leaving aside possible changes to Roth in the future, wouldn't 2) be more beneficial for those with many decades left?
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Old 05-10-2016, 12:31 PM   #22
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I've looked at it a few times and never pulled the trigger on Roth conversion because although we are in the 15% tax bracket now, most of our income is from capital gains. We have a chuck of it that we pay 0% taxes on since our ordinary income is so low. Doing a Roth conversion means we pay tax on cap gains instead. Social security income and ultimately RMDs will push us into the 25% tax on ordinary income in about 10 years.

It's actually worse - we aren't really in the 15% tax bracket on ordinary income. We're in the 26% tax bracket (our capital gains income triggers AMT on our ordinary income) and sometimes NIIT, add another 3.8%. Any Roth conversions would likely be taxed at a 29.8% rate as well as eliminating our 0% cap gains "bracket". Suddenly not so appealing to convert.

Our IRAs are only 10% of our retirement funds, so RMDs will not be large compared to our annual income (same with social security).

I'm focusing exclusively on reducing our capital gains annual income so that by the time we do have social security income and RMDs it won't have as large of an effect. Might still push us into the 25% tax bracket, but maybe some of the other high tax ramifications can be avoided including paying the highest Medicare rates.
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Old 05-10-2016, 02:07 PM   #23
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Originally Posted by AnonEMouse View Post
How do you account for the the differences in tax treatment of the future gains?

1) The gains are tax free now, but all future gains from it are taxable

2) Converted values and their future gains remain tax free "forever"

Leaving aside possible changes to Roth in the future, wouldn't 2) be more beneficial for those with many decades left?

I'm not sure we're understanding one another. So I'll go through my thinking in steps.

Roth vs. 401(k)
If your tax rate doesn't change, the after tax value of your Roth is identical to the after tax value of your 401(k). Paying 15% now and then never paying taxes again is identical to not paying 15% today but paying 15% on the entire account balance at the end.

So if your tax situation doesn't change you're basically indifferent between the Roth and the traditional 401(k) [inheritance issues excluded]

Gain Harvesting
As long as you stay within the 15% tax bracket all capital gains and qualified dividends are taxed at a rate of 0%.

So if I'm in the 15% tax bracket and I have a $200 investment that I bought for $100 I can sell it and immediately repurchase it tax free. I step up my basis from $100 to $200. I never have to pay taxes on that $100 gain. Any future gains or losses may be taxable or tax deductible.

Bringing both together
I can really only do one or the other transaction (or mix and match) while staying within the 15% tax bracket. Both Roth conversions and gain harvesting increase current income and push me toward higher brackets. So doing one reduces my ability to do the other dollar for dollar.

With that in mind, if I don't expect my future tax bracket to change I'm (mostly) indifferent between having a Roth and a traditional 401(k). And converting from a 401(k) to a Roth consumes my capacity to gains harvest tax fee.

So I have a choice. I can choose a Roth conversion which may or may not yield any benefit. Or I can harvest gains and permanently decrease my taxable asset value.

Caveats
Roth accounts have additional benefits over traditional 401(k) accounts not mentioned above. Because they don't have RMDs investments in Roth accounts remain tax-deferred for longer and can also be passed on to heirs.

Raising the tax basis of a security only conveys a tax benefit if that asset is ever sold in the future. If the asset is never sold, gain harvesting yields no benefit whatsoever.

At the same time, tax laws change and not always in the way we expect. The imposition of a VAT or carbon tax would mean that your Roth conversion gets taxed twice. It's not a certainty that future tax changes will benefit Roth accounts.
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Old 05-10-2016, 02:28 PM   #24
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Married couples may also want to consider the implications to a surviving spouse when deciding whether (today) to convert tIRA monies to a Roth or reduce basis in taxable accounts by taking advantage of the 0% LTCG rate. If a surviving spouse winds up in the 25% bracket (very easy given the loss of deductions and reduced brackets), then any remaining cap gains would be taxed at 15% instead of 0%. The tax rate for tIRA funds would go from 15% to 25%. A 15% difference in tax rate is more than a 10% difference, so it favors harvesting those LTCGs rather than using up "headroom" in the 15% bracket to convert to Roth.
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Old 05-10-2016, 02:47 PM   #25
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+1 I discount the future a lot, given the uncertainty. As Gone4Good pointed out, a dollar saved today is money in the bank. My reasoning behind not doing Roth conversions:

1. If I'm in a high tax bracket in my later years, it will mean that my portfolio has performed well and I have won the game, and I will happily write big checks to the IRS. OR I'm in a higher tax bracket as tax rates rose and I missed the boat.

2. If I'm in a low tax bracket in my later years, it will either mean that my portfolio has tanked, or that tax rates are lower. In either case, not doing Roth conversions earlier would have been the right decision.

3. If I'm dead, I won't be paying any taxes, so not doing the Roth conversions earlier would have been the right decision.
I fixed your statement
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Old 05-10-2016, 03:05 PM   #26
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We convert to the top of the 15% bracket. But it's a fairly small number due to rental income and 2 pensions. Our tax-deferred balances are quite large, so I've thought about converting into the 25% bracket. But it just doesn't seem to make sense for us.

I've modeled our future tax situation as thoroughly as I know how. There's no reasonable downside scenario under which RMDs will totally escape the 25% bracket. So converting what we can at 15% makes sense. But the probability of RMDs getting even partially taxed at 28% is sufficiently low that I see no compelling case to convert at 25%. Especially since the immediate impact is actually greater than 25% due to the impact on qualified dividends and capital gains. As we get closer to 70, we can certainly adapt as needed.

If I'm wrong, it will be due to very favorable market performance. So paying a couple percentage points of incremental tax will be no burden. Then again, if OP's CPA is correct about future tax rate increases, the impact could be quite a bit larger. My planning is always based on current tax law and reasonable estimates of indexed brackets, etc. If and when there are actual changes, I'll adapt the plan accordingly. I could easily envision flat/lower income tax rates plus new VAT. So I'm not inclined to change direction based on one CPA's opinion.

Early death of one spouse does change the analysis quite a bit. But we are both in reasonably good health. So the baseline plan assumes a reasonable life expectancy for both. Again, if our health status changes, we can adjust the plan at that time.

I've thought about CG harvesting instead of Roth conversions to fill out the 15% bracket. But since our expenses are mostly covered by pensions, rentals, and dividends, we simply don't sell much, if at all. When SS starts, we definitely won't be selling. RMDs, on the other hand, are inevitable. So converting is the current strategy, but definitely not beyond the 15% bracket.
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Old 05-10-2016, 05:02 PM   #27
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I have been converting to either the AMT threshold, the 250k AGI threshold, and maybe into the 28% bracket once (whichever is lower), for the past 3 years and will continue roughly the same for the next 6 or so years. This will get me almost out of the 25% bracket when RMD's hit along with SS benefits and a small pension at age 70. I have a very detailed program to calculate future withdrawals, taxes (federal and state), and portfolio values.

The value of Roth converting when the current tax rate will be the same as the future tax rate is that you are effectively moving a little of your taxable account value (an amount equal to taxes paid on the conversion) into the nontaxable Roth account. Numbers-wise, that's it. You save whatever taxes you would have paid had that money remained in a taxable account. So it's not as compelling as converting at 15% taxes now to avoid 25% taxes later.

For this (conversion into the 25% bracket) to make any sense, you need to have a large 401k/tIRA balance (large RMD's coming taxed at 25%), and a large taxable account balance (to live off of and pay Roth conversion taxes for the years it takes). So it certainly won't be beneficial to everyone.

As far as tax laws, all we an do is assume current laws will continue into the future. I do inflate tax brackets along with my portfolio and withdrawals and SS benefits. Beyond that, I'll wait until any changes are more certain before I modify anything. If anything, I lean towards expecting higher tax rates. I don't think Roth and tIRA accounts will be taxed wildly differently in the future (as in a tax that applies to Roth withdrawals only). As already mentioned, the survivor of a couple will see higher single tax rates. So I'm willing to push Roth conversions now.

I'll still have a substantial tIRA after all Roth conversions, sufficient to fill in the current 15% bracket for a long time after age 70. I'm not going to pay 25% taxes now when I could be paying 15% later! Plus I'll be out of taxable money before the tIRA is empty. So I'll have some flexibility still if tax laws change.
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Old 05-10-2016, 05:58 PM   #28
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Married couples may also want to consider the implications to a surviving spouse when deciding whether (today) to convert tIRA monies to a Roth or reduce basis in taxable accounts by taking advantage of the 0% LTCG rate. If a surviving spouse winds up in the 25% bracket (very easy given the loss of deductions and reduced brackets), then any remaining cap gains would be taxed at 15% instead of 0%. The tax rate for tIRA funds would go from 15% to 25%. A 15% difference in tax rate is more than a 10% difference, so it favors harvesting those LTCGs rather than using up "headroom" in the 15% bracket to convert to Roth.
Another consideration applies if you live in a community property state. Assets held as community property receive a full (not just half) step-up in basis upon the death of the first spouse. The surviving spouse would reset basis on all taxable accounts and real estate if properly held, as if he/she had just inherited all of those assets. We hold all assets in a trust that defines held assets as community property for this reason. Based on our circumstances, it makes better sense to avoid harvesting capital gains and instead continue with annual Roth conversions to fill the 15% bracket.

Bogleheads article on the step-up in basis:
https://www.bogleheads.org/wiki/Step-up_in_basis

Which states?
https://en.m.wikipedia.org/wiki/Community_property
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Old 05-10-2016, 06:16 PM   #29
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I do both. I have gains traded in the past but at this point I expect to exhaust our taxable funds while I am still in the 15% tax bracket so I do see much sense to accelerating that benefit.

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....I have no idea how your CPA has any clue what tax rates are going to do... that's a SWAG I wouldn't put any stock in. JMO.
+1 tax rates have actually fallen over time but who knows what will happen... to think they will increase is pure conjecture on his part.

ORP would have me converting a lot more than the top of the 15% tax bracket. If I went from the top of the 15% bracket to the top of the 25% bracket with Roth conversion my federal tax would be $20,131 (26%) of the $76,300 additional conversion. Too much for me since the tax on my Roth conversion to the top of the 15% tax bracket is only 9.7%. I'm loathe to pay that 26% even though I know that in the long run it may be a wise move.
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Old 05-10-2016, 06:33 PM   #30
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Another consideration applies if you live in a community property state. Assets held as community property receive a full (not just half) step-up in basis upon the death of the first spouse. The surviving spouse would reset basis on all taxable accounts and real estate if properly held, as if he/she had just inherited all of those assets. We hold all assets in a trust that defines held assets as community property for this reason. Based on our circumstances, it makes better sense to avoid harvesting capital gains and instead continue with annual Roth conversions to fill the 15% bracket.

Bogleheads article on the step-up in basis:
https://www.bogleheads.org/wiki/Step-up_in_basis

Which states?
https://en.m.wikipedia.org/wiki/Community_property
Wow - incredibly good point. I shall have to look into this.
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Old 05-10-2016, 08:12 PM   #31
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Assets held as community property receive a full (not just half) step-up in basis upon the death of the first spouse. The surviving spouse would reset basis on all taxable accounts and real estate if properly held, as if he/she had just inherited all of those assets.
Very helpful, thanks!
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Old 05-11-2016, 08:05 AM   #32
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Another consideration applies if you live in a community property state. Assets held as community property receive a full (not just half) step-up in basis upon the death of the first spouse. The surviving spouse would reset basis on all taxable accounts and real estate if properly held, as if he/she had just inherited all of those assets. We hold all assets in a trust that defines held assets as community property for this reason. Based on our circumstances, it makes better sense to avoid harvesting capital gains and instead continue with annual Roth conversions to fill the 15% bracket.

Bogleheads article on the step-up in basis:
https://www.bogleheads.org/wiki/Step-up_in_basis

Which states?
https://en.m.wikipedia.org/wiki/Community_property
Wow - even though I've lived all my adult life in a community property state, I did not know this. I hadn't really thought much about the basis of investments in brokerage accounts after one spouse passes.

I knew a US citizen surviving spouse could inherit with no estate taxes, and figured a 50% step up in basis, but didn't know about the 100% step up in JTWROS accounts or jointly owned property like a house. Better make sure all the titles are correctly titled.
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Old 05-11-2016, 09:27 AM   #33
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I use the variable amount slider on the Fidelity Roth conversion evaluator. Based on my inputs and state taxes, I can vary where it shows optimum amount to convert. I have never exceeded the 15% bracket, but may by just a little when it comes to transferring Vanguard Admiral minimums. I know it's silly talking about a few basis points but I am wired that way.

There is a radio show in Pittsburg called The Lange Money hour where they have back episodes where you can download. He has mentioned this topic before with well know IRA experts.

The Lange Money Hour: Where Smart Money Talks - Radio Show with James Lange, CPA/Attorney

edit formatting and clarity
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Old 05-11-2016, 10:16 AM   #34
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.......................

It's actually worse - we aren't really in the 15% tax bracket on ordinary income. We're in the 26% tax bracket (our capital gains income triggers AMT on our ordinary income) and sometimes NIIT, add another 3.8%. Any Roth conversions would likely be taxed at a 29.8% rate as well as eliminating our 0% cap gains "bracket". Suddenly not so appealing to convert.

.................................................. .....................
Might be even worse.....if you're in AMT land, the exemption phases out w/
increasing income in some range so that it's 26% + 25%(26%) = 32.5%
+ NIIT. You can put numbers in Taxcaster to verify.
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Old 05-11-2016, 11:06 AM   #35
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Another consideration applies if you live in a community property state. Assets held as community property receive a full (not just half) step-up in basis upon the death of the first spouse. The surviving spouse would reset basis on all taxable accounts and real estate if properly held, as if he/she had just inherited all of those assets. We hold all assets in a trust that defines held assets as community property for this reason. Based on our circumstances, it makes better sense to avoid harvesting capital gains and instead continue with annual Roth conversions to fill the 15% bracket.

Bogleheads article on the step-up in basis:
https://www.bogleheads.org/wiki/Step-up_in_basis

Which states?
https://en.m.wikipedia.org/wiki/Community_property
Thank you for such a good information that I never knew.

I live in one of the community property states, California. We have some stocks acquired thru ESPP. When we sell, we will pay the 15% discount as ordinary income. The gain above that as short/long term capital gain.

If one of us passes, will the surviving spouse move the new step-up basis in full, or the 15% ordinary income still owed by the time when surviving spouse eventually sells it?
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Roth conversions beyond the 15% bracket
Old 05-11-2016, 11:58 AM   #36
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Roth conversions beyond the 15% bracket

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I knew a US citizen surviving spouse could inherit with no estate taxes, and figured a 50% step up in basis, but didn't know about the 100% step up in JTWROS accounts or jointly owned property like a house. Better make sure all the titles are correctly titled.
Be careful.... Property held in Joint Tenancy only gets a 50% step-up in basis. It has to be held as Community Property (in a community property state) to get a 100% step up. Here's a California attorney's explanation.
http://www.blog.chubblawfirm.com/201...in-california/

Nolo article on how property title should read:
http://www.nolo.com/legal-encycloped...hapter6-5.html

To be safe, we hold everything in a revocable trust that defines ownership as community property, and the trust provides other benefits as well.
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Old 05-11-2016, 01:07 PM   #37
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Roth conversions beyond the 15% bracket

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Thank you for such a good information that I never knew.



I live in one of the community property states, California. We have some stocks acquired thru ESPP. When we sell, we will pay the 15% discount as ordinary income. The gain above that as short/long term capital gain.



If one of us passes, will the surviving spouse move the new step-up basis in full, or the 15% ordinary income still owed by the time when surviving spouse eventually sells it?

I'm not an attorney or tax advisor, but my understanding is that for a qualified ESPP if the employee dies, income on the original purchase discount is reportable to the decedent in the tax year of death. If the spouse dies first, the income portion is not yet taxed. The tax basis is stepped up according to how the stock was held (separate property, joint tenancy or community property).

The tax code has a host of examples at the end of this excerpt: https://www.law.cornell.edu/cfr/text/26/1.423-2
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Old 05-12-2016, 07:51 PM   #38
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Roth conversions beyond the 15% bracket

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I generally find Roth conversions difficult to justify at any tax bracket.
+1. I just generally like the idea of letting maximum money compound longer and then managing taxes vs. paying some tax but but reducing the eventual nest egg. Maybe I'll be sorry but here is a solid article on the topic that influenced my thinking:

http://www.caniretireyet.com/roth-ir...ersions-needs/
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Old 05-12-2016, 08:15 PM   #39
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+1. I just generally like the idea of letting maximum money compound longer and then managing taxes vs. paying some tax but but reducing the eventual nest egg. Maybe I'll be sorry but here is a solid article on the topic that influenced my thinking:

Roth IRAs and Roth Conversions: Who Needs Them? - Can I Retire Yet?
Here's the catch I find in the logic from that article:

Quote:
Suppose you’re in the 15% tax bracket and you have $5,000 to put to work in a retirement account. In a Traditional IRA account that gives you a starting balance of exactly $5,000, because the contribution is before taxes. But in the Roth account, which is after taxes, you’d have just $4,250, after paying your 15% taxes first from the initial sum.
Don't pay your taxes out of the conversion. Instead, pay it from a taxable account. That way you'll have $5,000 is the Roth, forever growing tax free.
Quote:
Assume you’re getting about a 7% return. Ten years go by, and your investments have doubled in value. Now you have $10,000 in your Traditional account and $8,500 in the Roth.

Now it’s time to withdraw and use the money. (We’ll ignore various time limits and penalties which are irrelevant for this example.) The Traditional account is taxable, so when you pull out the $10,000, you must pay your 15% tax, leaving you with $8,500. The Roth however is tax free, so when you pull out the balance, you get to keep the full amount. You wind up with $8,500, just like the Traditional.
By paying out of pocket, you now have $10K in your Roth, compared to $8500 after taxes in the tIRA. You have $750 less in your taxable, which would've also doubled to $1500, but you would pay cap gains tax on that $750, or $112.50.

The net is, on a $5000 Roth conversion you came out $112.50 ahead. Not a huge amount, but it is over 2%, and of course we usually are talking about having a lot more in an IRA. I'll take any advantage I can get.
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Old 05-12-2016, 10:15 PM   #40
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Yeah, but all that ignores the real reason to do Roth conversions... you are temporarily in a lower tax bracket... the last 3 years I've paid about 10% on my Roth conversions... I'm sure that my tax bracket once pensions and SS are online will be 25%... it certainly will not be less than 15%.. so the real kick is the lower tax rate.
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