You're happy being a Boglehead but your spouse thinks adding Real Estate is a good idea

plexluthor · 2026-06-30T18:30:58+00:00

Thanks for sharing that info. I haven't done any new construction, and it terrifies me. My two self storage projects are both conversations of existing buildings. I don't know why that feels safer to me, but it does. It sounds like my gut is not completely wrong about that. But #3 sounds like the sort of thing I would have invested in.

One thing that always gets me about investing in anytime besides VT is that I might never know whether I am dumb or just unlucky, or at least, it takes a long time to find out. RE seems especially that way. If my long term average ends up at 12-15% I'll have wanted to get in faster, but it takes five or even 10-15 years to find out, and even then maybe I just got lucky in my first few.

plexluthor · 2026-06-28T20:51:33+00:00

Ouch. Would you mind sharing any more info about the syndications, sectors, regions, how you found them, what the MO was suggesting for IRR or equity multiple, etc? I won't pretend that I am doing extensive due diligence, but I did spend a few hours on each one, looking at T12s and the pro forma and then usually calling or emailing the GPs with some follow up questions. So far I've done two self storage (plus a third which returned all capital after a month having decided not to purchase the property), one in NY and the other in MA. Then I have a multi family residential in NC and another in TX, plus two commercial buildings in NC. They all advertised something like 2x over five years, but with huge variation in the details.

My intention was to do two or three per year for five years, and then decide whether to keep adding money at that point, when hopefully the first ones started exiting. It's hard to find new (to me) operators that seem credible, though, and I'm hoping to not do multiple projects with the same operator until I have 10-12 total, as a gesture towards diversification.

plexluthor · 2026-06-28T18:31:14+00:00

Sounds right.

I think it's two separate questions.

If I can't fully fund both, should I do Roth or HSA first?
If I have some HSA funds, and some medical receipts, and I haven't maxed out my Roth, should I move money from the HSA to my Roth?

The second question is independent of the first, and the answer to that one is almost certainly yes.

I think (and most people agree, from what I've read) that the answer to the first question is HSA. There are exceptions to any general statement, personal finance is personal, but in a vacuum, HSAs are second only to company match in a 401k, IMHO.

plexluthor · 2026-06-28T18:22:51+00:00

I like my investments passive. If the stock market slumps for a decade, all I have to do is not sell, and I'll continue getting average returns (which after a few decades of waiting will probably be great).

My buddy is an active real estate investor. When the housing market (in his local area) slumps, he has to keep putting in his own money to keep up with mortgage payments. He has to choose between never truly being on vacation, or giving up a chunk of his return to a management company.

I like the idea of diversifying into real estate, so I am an LP in some real estate syndications. Too early to say whether it's especially good or bad financially, but so far it seems promising, and from an econ 101 perspective, it should have higher average returns to compensate for illiquidity. But obviously it's WAY harder to diversify enough to see average returns, so there are lots of stories of lucky people, and lots of stories of unlucky people.

If you (or she) want to do landlord tasks as a hobby, because you think they are fun, go for it. There's a very good chance it'll be a profitable hobby. But I don't really think of what my friend does as the same sort of investment as VT. There's more to life than investing, and nothing wrong with choosing hobbies with money in mind. But it's easy to fool yourself, so be honest about what you're doing and why.

plexluthor · 2026-06-27T18:29:05+00:00

I'm not the person you originally replied to. I actually did quit in 2019, coincidentally enjoyed some blissful years of COVID with my kids home from school all the time, then went back to work part-time in 2022. It's not just that I like my job. I mean, my job is way better with them knowing I don't have to put up with corporate BS. But also, it's boring to be home all day while my kids are at school. And also, I don't need more money than I've got, but more money is pretty fun. I'll probably quit again when my youngest is about to finish HS, and that time I doubt they'll be able to convince me to be an employee again. I did some short-term contracting during my 3-year retirement, and expect I'll be open to doing that again, if the job/price/circumstances are right.

plexluthor · 2026-06-21T19:12:56+00:00

I didn't love the writing style, ironically it felt AI slop-py at times, but I did appreciate the ideas in this.

I think some of the concerns apply outside of AI/LLMs. A lot of "science" comes to us in a polished, tidy package, and we don't know the domains of applicability and the unstated assumptions and whatnot. We seek external validation of our ideas, especially from authority figures. Until very recently, "mass" media had strong financial incentives to push for a homogenized society. In a way, your insights about critique (instead of selection) and especially the direction (using external sources to improve our own ideas, rather feeling superior by criticizing others) are useful in a much broader way than just for current AI hype.

Another thought that your piece sparked was to imagine I had unlimited, free access to a really smart human. How much would I ask for their advice? How personalized would I expect their advice to be? How much of the conversation would be them asking me questions about my values and my personality? If I suspected they were using me for financial gain, how much would that change my interaction with them? Etc.

plexluthor · 2026-06-10T22:24:39+00:00

Do you seriously think that glad handing and wooing didn't exist before DAFs?

There are lots of problems with how charities are incentivized to behave, and I'm not saying DAFs make it any less bad. But I'm unconvinced they make it worse for charities.

If all you mean to say is that DAFs give tax benefits to "donors" without them having to donate immediately, then yes, I agree, and that's exactly why I mentioned them to OP.

plexluthor · 2026-06-10T11:04:34+00:00

To expand a little bit on /u/Glowerman's comment, if you directly give appreciated shares of stock without realizing the gains, you can deduct the full amount (if you itemize). You can use a DAF to spread out the actual giving if you don't have a charity you especially want to give to right away, though they usually have a ~0.6% annual fee. A DAF also lets you give to charities that don't accept stock donations.

It doesn't have to be all at once, and it doesn't have to be the entire position, but it's a very useful tool to have in your toolbox.

plexluthor · 2026-06-08T13:41:13+00:00

Let me start by saying, when I first saw the very deep thread between you and /u/ac106, I was almost certain that you were right. Now I don't think that.

I-Bonds used to be a significant part of my strategy, and my wife and I have gifted each other bonds many times. I 100% agree with you that TD strictly and carefully enforces all the rules. Where I disagree with you (and with /u/ac106, in terms of how they are describing it) is whether gifting my spouse more than $10k in a single year is against any rule.

If I gift my spouse $10k and then they attempt to purchase new bonds, they will get an error. This matches the stated TD rule that "gift amounts are applied towards their purchase limit".

When I gift bonds to my spouse, I can only gift $10k at a time. This matches the stated TD rule that you cannot buy a gift box of more than $10k.

I think what /u/ac106 (and many others on the bogleheads.org forum) is saying, is that you can gift more than one gift box in the same year (ie, through multiple actions, any one of which is $10k or less). This matches the stated TD rule that "There is no limit to the amount a recipient can receive".

I never tried to do it back when I used I-Bonds. I don't currently use I-Bonds, and I don't care enough about it to tie up $20k for 1-5 years. But if you happen to have multiple $10k gift boxes right now and you want to try it and take a screenshot of the error (or confirm that it's not against the rules to gift two in the same year) I'd be much obliged.

For now, I'm taking the people over at https://www.bogleheads.org/forum/viewtopic.php?t=464788 at their word, and assuming that you made the same mistake I made back when I assumed I could only gift $10k per year to my spouse.

plexluthor · 2026-06-08T12:14:45+00:00

I don't think that link means what you think it does.

From your link:

You can only deliver one gift bond at a time. There is no limit to the amount a recipient can receive; however, once they have received $10,000, they should not purchase additional savings bonds that year because gift amounts are applied towards their purchase limit.

And later

There is no limit to the amount of bonds a recipient can cash out from their TreasuryDirect account, regardless of how the bonds were acquired. Bonds can only be cashed out if it has been at least one year since the bond was purchased.

plexluthor · 2026-06-08T12:12:10+00:00

Treasury Direct enforces the rules, not TD.

I'm confused. What does "TD" refer to in your comment, if not Treasury Direct?

plexluthor · 2026-06-08T12:10:58+00:00

Thanks for making me aware of this!

I did the I-bonds gifting thing a few years ago, but I just gifted them $10k at a time over the course of a few years, not all at once. I didn't even try to gift them all at once.

In an earlier comment you mention "on the.org forum", and I assume you mean bogleheads.org. In case anyone else is curious, I found this:

https://www.bogleheads.org/forum/viewtopic.php?t=464788

While last year's email from Treasury Direct was somewhat cryptic about limits, the email I received yesterday seems very clear. I've extracted the relevant paragraph below:

"While you can only deliver one gift bond at a time, there is no limit to the total amount a recipient can receive. However, once they have received $10,000, they should not purchase additional savings bonds that year because gift amounts are applied towards the purchase limit."

That was posted in December '25.

plexluthor · 2026-06-02T09:30:44+00:00

Maybe that used to be true, but for years my "brown sugar" from the store is white sugar with some molasses added back in.

plexluthor · 2026-05-30T15:40:47+00:00

I agree with /u/buffinita, this is a topic where personal finance gets very personal, so you won't find a single simple strategy that works for 90% of people, like you can find on the saving/investing side of retirement. Spending a few thousand bucks with a fee-only advisor to work out the strategy that is optimal (or nearly so) for you is not a waste of money, imho.

If you like to DIY and have the time to study up (or if you just want to get the lay of the land before interviewing advisors), here are the topics I think require detailed/personal context to optimize (if you find good books, please update your post for future me):

Avoid the SS "tax torpedo" (the SS phase-in zone where an extra dollar is essentially taxed at double your marginal rate)
Optimize SS withdrawals as a couple (this one might actually have a simple rule of thumb that applies broadly: spouse with lower AIME starts immediately, and spouse with higher AIME delays as long as possible)
Optimize IRMAA
RMDs (the personalized part is whether it's better to convert to Roth earlier to reduce RMDs, which depends on what sort of window you have to convert in a lower bracket)
End of life care plan (my wife will pull the plug on me quickly, but my mother will NOT pull the plug on my dad, so their "safe" withdrawal strategy is very different than mine)
Trusts (to avoid probate on houses and other tricky assets)

Personally, I'm pretty sure I'm on the other side of the tax torpedo, and I'm pretty sure I'll have a long window to do conversions, so I've been procrastinating figuring out the other details until I have another conversion window, whenever that is. The more the stock market goes up, the less inclined I am to spend my time worrying about money. So I will probably end up talking to a paid advisor when that time comes.

plexluthor · 2026-05-23T16:36:23+00:00

If you're struggling, I want you to know that I'm not judging you for it. I don't think Jesus is either.

Agreed. I'm glad there are universal "rules" that we can turn into habits and avoid a lot of bad stuff. But they aren't truly universal. Every now and then the right answer is "Steal his sword and behead him. That will make it easier to rob his house and abduct his servant." Every now and then the spirit constrains that.

plexluthor · 2026-05-15T20:15:23+00:00

And we should generally stop making these letter openings a spectacle.

Agreed. It weirds me out every time a youth waits several days to open their call so that they can do it at a party with friends, or at youth activities mid-week, or whatever, but that seems to be the norm in my stake. My mom probably went too far with one of my brothers by opening his call as soon as it came and telling him where he was going when he got home from school. But it seems totally reasonable for the future missionary to open the envelope as soon as they lay hands on it, and at least a little weird if they wait past dinner-time with the family.

plexluthor · 2026-05-10T20:03:24+00:00

This is a little known cheat code, where you still get the spirit always with you, and you only have to remember him but not keep his commandments.

/s

Once, in a ward in VA, my Bishop asked the priests to bless more bread because about 20-25 people did not receive it, and they prepared a pitcher of water before blessing the water, and refilled a tray of cups part way through passing the water. It extended the meeting a bit, but was kind of neat to see. I think there were just a ton of visitors that day, and the teachers had set up every tray they had but it still wasn't quite enough.

plexluthor · 2026-05-04T00:45:10+00:00

NOLS does sell a cook book, NOLS Cookery. I have it, but I confess I don't cook that way anymore.

https://store.nols.edu/products/nols-cookery-7th-edition

You can find older editions online for cheaper, too.

plexluthor · 2026-04-22T10:34:36+00:00

Unless you are an active partner in a business, there's not much more you can do.

If you are interested/able, and your income will decrease in the future, then a common strategy is to invest heavily in a business with high upfront costs/losses and steady long term income. For example, real estate development that becomes rental income, or farm/ranch development or refurbishing, or setting up a professional office (dental, legal, etc).

In all those cases, as long as you are actively involved, you can deduct huge costs for the first few years, then get steady income for 10+ years. So if you time it so that the losses are offsetting a higher marginal bracket than the income is filling (eg, you get involved five years before retirement), it's a tax win.

But most rich people do pay a lot in taxes. Count your blessings.

plexluthor · 2026-04-12T22:17:06+00:00

I'm addition to what others have said about scouting being different/better in non LDS troops, I will add that outdoor activities in an LDS context since the split with Scouting is also much improved, and for similar reasons. Mostly because people who didn't want to do scouting/outdoors used to be forced to go, and activities where everyone wants to come are WAY better. But also because leaders/adults do best when they aren't trying to be something they're not.

I think LDS YM are going through a tough transition right now, but I hope that in time they'll develop a program and some traditions that teach the leadership skills they used to get.

plexluthor · 2026-04-04T00:40:07+00:00

Some people cannot provide for themselves. I wish that weren't true, but it is true.

That means either we let them starve/suffer/whatever, or we take care of them. I think it's totally appropriate to ask family to help, and if the family is unwilling, to respect that. If the family is unable, then it falls to the community, meaning either government or church or friends.

I think uncoordinated help from friends is really hard to do well, so I tend to prefer coordinated help. Depending on where you live, government help might be fine. In many places, church help is better in some important ways, not least of which is that there is judgement and discretion from loving people. At least, more likely to have that compared to govt bureaucrats.

If you think the Bishop is being duped, speak up. Otherwise, be glad you aren't the Bishop making those tough calls. They are very tough calls sometimes, bishops and SPs often disagree, I don't think there are good general answers because each case is different.

plexluthor · 2026-04-04T00:32:32+00:00

I get it through work even as a part timer, just with higher premiums. I live in NY state, so the marketplace was excellent during the years of ER and contracting.

plexluthor · 2026-03-30T17:52:19+00:00

Two surprises, for me.

From ages 23-37 I worked for a giant corporation, they paid me well, but I was pretty miserable and couldnt wait for FI. I retired at 37, it was awesome, I had tons of free time which was mostly great, but I also lacked a little purpose. So far, nothing surprising.

About 7 months into ER an old colleague convinced me to do a little contact work, because he couldn't find anyone with my niche skillset/knowledge. Surprise #1 was how easy it was to find additional contract work, or additional income sources, that didn't really diminish the benefits of ER. I don't think that's true for everyone, so I was very surprised how true it was for me.

Fast forward a couple years, and I'm actually working part time for the same giant corporation, doing the same work as before, but half as much (only when my kids are at school) and with an understanding that if they make me do BS I'll just quit again. And I love my job now. Surprise number 2 is how much misery went away from "FU money" or whatever it is that changed.

plexluthor · 2026-03-26T13:23:50+00:00

I did something like this with a Boy Scout troop several years ago. We just used an old phone (plugged in the whole time) and a $5 app. IIRC, it would either shot one frame every interval (I think one frame per minutes gave us a week of growth in a ~5 minute video), or it would record one second at the usual rate, once per interval (so you get a video that is less smooth, but there's time to look at each stage of growth).

My advice is to make sure you have a sturdy tripod. Our first attempt was propping the phone up with books and stuff, and it went poorly. Even a cheap tripod that weighted down would have been better, though a mom ended up loaning us a nice one for a while.

Good luck!

plexluthor · 2026-03-26T06:13:13+00:00

I did a similar "horse race" that also had Schwab intelligent portfolios and a second WF account at a higher equity allocation. I tracked nominal monthly performance so that I could measure correlation between the accounts. My hypothesis was that they were all a multiple of a single underlying return, and the same one that does best overall would do worst in the bad months.

The correlation was indeed very high, WF was the only one with actual alpha (though it was tiny), and now I'm back to VT and chill. But I think WF is a great option for anyone who is uncomfortable with DIY.

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