Question about bond placement (asset location) and couple side questions

hotwired

Recycles dryer sheets
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Jun 9, 2008
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Over past two Januarys I’ve sold two 7-unit apartment buildings (and am saddled with CAP gain and depreciation recapture) The sale gave us an incredible 10-12 year IRR of 35% and 42% respectively (many of those years unleveraged) but also created a sickening tax bill. (I’m not one of the cool kids who does the 1031 exchange or puts my apartment buildings in my IRA…I’m just a lovable lout that bought rundown buildings in my home town). From those proceeds, I created a bond ladder with couple other income producing assets (BKLN, JAAA) to nudge the overall yield of the ladder upward. 10 year ladder, with 12-40K maturing each year. THEN I put about 100K out to years 27-30 both zero treasuries and TIPs. My thought was that it was a Win/Semi-Win. If yield curve UNinverts, which it will, and that pops long term rates a little higher, I’ll lose money short term, but I’ll have a real 2.25% return on about 70K and a 4.8% nominal return on 30K worth of zeroes for the next 27-30 years. Sort of “longevity annuity” but fully funded! A little sloppy. Some are low coupon TIPs which will total return well, but not throw off much income. Also some regular treasuries, a couple of agencies at 6% but heavy on TIPS. Some high coupon, some low (.125% to 2.43%). I bought most of the TIPs with a real YTM of 2.2% and above. I’ve also got 120K in iBonds, 70K with 1.3% inflation factor, 50K at .9%. I may redeploy the .9’s next year with a “fresh” slate tax wise. I’m also STRONGLY considering sheltering some of the interest by trading in some bonds for MYGAs if it’s not too late. I’ve been hemming and hawing over whether to use Stan the Annuity Man or a local person. Also for clarity, this bond ladder only represents 20% of our assets. We’ve got 2m~ in IRAs, 401K, annuity and other funds, and 400K value of remaining 2 rental properties which net 30-35K per year.

I should note that we more or less adhere to a 50,30,10 stock bond RE mix. We have an AUM advisor which I’m trying to slowly get my wife to agree to “fire nicely”. As we’re in retirement now, I’m certainly not going to pay someone 1% a year to manage a bond ladder yielding 4-5% a year. But it gives her security and that’s OK. We have 2-3% in crowdfunded real estate, mostly hard money lending funds, and 1% in crypto (my return has been over 3,000% so I’ve already taken out 30x what I put in and am playing with house money. I’m no crypto genius, I just happened to do a LOT of reading and bumped into it in 2013. Lucky me.

So question: My wife and I have sizable solo 401K’s with Vanguard. They don’t allow brokerage accounts, only Vanguard Funds. But I thought it MIGHT be smart to move the 401ks to Fidelity, put as much of the bond ladder in those 401ks as possible, then use the taxable account to buy Index funds (I just do vanguard total US market, total ex-su then tilt with vanguard small cap value). My caveat is that this is a NON rolling (for the most part) bond ladder, and we’ll need to spend each rung as it comes due. Does it make sense to “shelter” these bonds from interest when we’ll have to yank it out and pay tax as regular income? One idea: I do this “switch” but each year when I need to cash in a rung, sell some index fund from the taxable for the amount I need, then re purchase that amount in the 401K to “replace it”. This way I’m cashing in the rung, it’s done its job, no tax on interest, no tax on withdrawal, just whatever capital gain OR loss from the stock index fund position. If I’ve “sold low” no problem, just take the tax loss, wait 31 days, re-buy it with the matured bond proceeds inside the 401K.

Also, any thoughts about Stan the Annuity Man? Just the cheesiness of his title makes me cringe but he seems to be the real deal and I haven’t heard anything bad about him. Someone that visible that was cheating people or doing a lousy job ought to have a reputation by now and I haven’t seen anything but glowing recommendations. And he really seems to “dig his craft”. I respect that.

Also considering adding a bit more into these floating rate funds and AAA CLO fund. I know the basics of CLOs (lower and lower tranches then finally an equity tranch which is the riskiest like OXLC, and the like.) But as look over their long term history, I don’t see any disasters on the "higher" tranches. Yes, some credit risk as the bonds are “junk” territory, but short term, actively managed. I have 25K in JAAA and same in BKLN which I use as a little boost to my bond ladder (400K-ish). I understand if rates go down, or we get a recession there will be some defaults, but what is the risk here? Is it 5-8% drawdown or 20% drawdown?

Thank you in advance. I hope this was clear enough!
 
It is a bit long. Maybe summarize the questions at the end. Also what are your ages? FIREd? Goals? It may all have been in there but couldn’t bring myself to read it all. Sorry,
 
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Putting bonds in tax sheltered and equities in taxable is a common strategy. The idea to sell equities from taxable and repurchasing in tax sheltered makes a lot of sense. It is also a common strategy.

If you want annuities, there are only two types commonly recommended: MYGA and SPIA. I'm no annuity expert, but I have seen recommendations that one should wait until your 70's to consider a SPIA. I'm not that old yet. My current thought is that I will never buy an annuity. I'm a simple 3 fund person (VTI, VXUS, BND).

I try to just keep it simple and take what the market gives.

Have you considered Roth conversions?
 
My question posed a bit simpler:

My wife and I are "semi retired" having just unloaded most of our apartment buildings. We are selling slowly, to keep as much of the capital gain in lower bracket. I should note that we more or less adhere to a 50,30,10 stock bond RE mix. We have an AUM advisor which I’m trying to slowly get my wife to agree to “fire nicely”. As we’re in retirement now, I’m certainly not going to pay someone 1% a year to manage a bond ladder yielding 4-5% a year. But it gives her security and that’s OK. We have 2-3% in crowdfunded real estate, mostly hard money lending funds, and 1% in crypto (my return has been over 3,000% so I’ve already taken out 30x what I put in and am playing with house money.

From the proceeds of our rental property sales, I created a bond ladder with couple other income producing ETFs (BKLN, JAAA) to nudge the overall yield of the ladder upward. It's basically a 10 year ladder, with 15-40K maturing each year. THEN I put about 100K out to years 27-30 both STRIPs and TIPs. My thought was that it was a Win/Semi-Win. If yield curve UNinverts, which it will, and long rates rise, I’ll lose money short term, but I’ll have a 2.25% real-return on about 70K TIPs and a 4.8% nominal return on 30K worth of STRIPs for the next 27-30 years. I am looking at in as sort of a “longevity annuity”!

So question: Bonds are in our taxable brokerage churning out a ton of taxable interest. This ladder is non rolling. We'll cash in each "rung" as it matures. I want to shield some or all of the interest if practical. I could do a "swap" of sorts and buy the bonds inside my IRAs, but then I've got to pay ordinary income tax on it as I withdraw it, so that doesn't make sense to me. (we do also have ROTHs so we could stash a few years in those) or I could cash in the bonds and buy MYGas then at least I only pay tax as I cash them in.

What would you folks do?

Thank you for all your input.
 
"So question: Bonds are in our taxable brokerage churning out a ton of taxable interest. This ladder is non rolling. We'll cash in each "rung" as it matures. I want to shield some or all of the interest if practical. I could do a "swap" of sorts and buy the bonds inside my IRAs, but then I've got to pay ordinary income tax on it as I withdraw it, so that doesn't make sense to me. (we do also have ROTHs so we could stash a few years in those) or I could cash in the bonds and buy MYGas then at least I only pay tax as I cash them in."

Brokerage - generates taxable interest payable each year, principle is not taxed at maturity.
Traditional IRA - generates deferred taxable interest not payable until withdrawal of funds, principle is taxed at withdrawal of funds. RMD rules apply when reaching the target age as defined by IRS.
Roth IRA - generates non-taxable interest, and at maturity any withdrawal of principle is also not taxed.
The only 'advantage' to using MYGAs is that you pay taxes on principle and interest when the annuity matures. A CD in a T-IRA matures and you defer taxes until you withdraw the principle and interest. So you avoid the taxation time-bomb inherent in T-IRAs.
I'd use the Roth to hold the MYGA if that is allowed by the IRS.
 
...So question: Bonds are in our taxable brokerage churning out a ton of taxable interest. This ladder is non rolling. We'll cash in each "rung" as it matures. I want to shield some or all of the interest if practical. I could do a "swap" of sorts and buy the bonds inside my IRAs, but then I've got to pay ordinary income tax on it as I withdraw it, so that doesn't make sense to me. (we do also have ROTHs so we could stash a few years in those) or I could cash in the bonds and buy MYGas then at least I only pay tax as I cash them in.

What would you folks do?

Thank you for all your input.
Bonds should be in tax-deferred accounts as both tax-deferred account withdrawals and bond interest are ordinary income. Having stocks in tax-deferred accounts is changing tax preferenced income from qualified dividends and long-term capital gains into ordinary income.

Easy to fix... sell bonds in taxable ccount and buy stocks with proceeds and do the inverse in taxable account. Assumes no significant unrealized gains on the bonds.
 
Putting bonds in tax sheltered and equities in taxable is a common strategy. The idea to sell equities from taxable and repurchasing in tax sheltered makes a lot of sense. It is also a common strategy.

If you want annuities, there are only two types commonly recommended: MYGA and SPIA. I'm no annuity expert, but I have seen recommendations that one should wait until your 70's to consider a SPIA. I'm not that old yet. My current thought is that I will never buy an annuity. I'm a simple 3 fund person (VTI, VXUS, BND).

I try to just keep it simple and take what the market gives.

Have you considered Roth conversions?

Bonds should be in tax-deferred accounts as both tax-deferred account withdrawals and bond interest are ordinary income. Having stocks in tax-deferred accounts is changing tax preferenced income from qualified dividends and long-term capital gains into ordinary income.

Easy to fix... sell bonds in taxable ccount and buy stocks with proceeds and do the inverse in taxable account. Assumes no significant unrealized gains on the bonds.
That was my first thought (swap by selling and buying). However, these bonds are a "bond ladder" which will be used up, starting this year. So right NOW I'm paying taxes on the interest but as I use up the money (selling bonds) it's tax free other than any little bit of appreciation they might enjoy as FED lowers rates. If I "put" them in the tIRA, suddenly that same 30K that was tax free is now taxed as regular income. Granted, I could do this swap in ROTHs but we don't have QUITE enough "room" in the ROTHs (350K combined). Though as I type this, we could stuff the ROTHs first, then either leave the rest "naked" in the taxable or put the "later rungs" in tIRA...I'm probably overcomplicating this, but alas it's what I do to keep life interesting! Love to hear your further thoughts on the "need the money starting now" issue.
 
You can just reverse the swap when a bond matures if you need the maturity proceeds for spending. Let's say a $100 bond matures in the IRA but you need $100 for spending.

In the IRA use the $100 maturity proceeds to buy $100 of stock and in the taxable account sell $100 of stock and use the sale proceeds for spending.
 
I actually alluded to this sort of thing in my first very verbose post. I can see this working, unless of course we're in the middle of a bear market and cashing out a piece of the taxable stock fund would cause a permanent loss of capital. But of course I have optionality here... I can just pay the tax with an IRA withdrawal and allow the stock to recover, in a bear market scenario. (Furthermore if I have a chunk of the ladder in our Roth iris, that gives me further optionality.)

Thank you for reminding me about this option!
 
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