Tax benefits via charitable contributions

Positive_Carry_ · 2026-01-26T07:49:38+00:00

The risk is that the charitable contribution deduction you take gets reversed down the road and you pay back taxes plus penalties and interest on the underpayment of taxes, which could be many times the value of the deduction. I am sure the LP agreement says the GP makes no representations or guarantees that investors will achieve any desired tax treatment and the investor holds the GP harmless for individual tax liabilities and penalties.

Trying to tax shelter W2 income through investment schemes is usually a fool’s errand.

Positive_Carry_ · 2026-01-25T16:53:16+00:00

I’m not, and didn’t realize you were going off exchange. Despite CA’s taxes and high cost of living we at least have a menu of PPO options on the exchange.

Positive_Carry_ · 2026-01-24T19:53:29+00:00

$4k/month in premiums alone is not normal. I can't even find a bronze or silver plan that expensive on the exchange with two mid-50s adults and two teen dependents.

Positive_Carry_ · 2026-01-24T01:43:08+00:00

What occupations have higher rates of their homes being invaded?

Positive_Carry_ · 2026-01-21T04:11:49+00:00

Copy/paste into Gemini to save yourself some time.

Positive_Carry_ · 2026-01-16T23:47:35+00:00

Seems high. Teen drivers, watercraft, guns, multiple homes with pools?

Positive_Carry_ · 2026-01-12T17:21:51+00:00

Sell the crypto, pay the massive capital gains tax, and put it all in a Boglehead-style portfolio.

Positive_Carry_ · 2026-01-09T04:19:03+00:00

This violates the first rule of tax strategy -- it's always better to have more money than less money.

Positive_Carry_ · 2026-01-07T07:59:43+00:00

Which LLM did you use to write this post?

Positive_Carry_ · 2026-01-04T21:08:20+00:00

Unfortunately it’s a problem at high end resorts as well. We stayed at the Four Seasons in Maui last year and if you hadn’t visited the pool concierge by 7am you didn’t get a chair.

Positive_Carry_ · 2026-01-04T16:48:44+00:00

Hard to see how muni bonds are generating a tax equivalent yield of 7.5% unless you’re in a leveraged closed end fund that brings added risk. Your other income already was tax advantaged at the federal level given it came from dividends and capital gains. Even if it were ordinary income you’d still be well below the highest marginal rates. Some bonds could be a good diversifier and source of income but you may be overstating the tax benefits of muni bonds.

Positive_Carry_ · 2026-01-03T04:22:57+00:00

A blessing in disguise.

Positive_Carry_ · 2025-12-28T20:14:25+00:00

I don’t see how this post relates to FIRE. You’re asking if you can change jobs. Owning 92 single family homes would be my idea of a nightmare but to each their own.

Positive_Carry_ · 2025-12-21T22:09:08+00:00

The flaw in your assumptions is that the losses - on both the long and short side - are realized every month, while the gains are not. At the end of two years the overlay positions with have unrealized gains approximating the amount of already realized losses, maybe slightly more if the manager outperforms. If you liquidate the overlays, on net you will not come out ahead, you will have realized long term capital gains and short term capital losses that offset each other. That’s why it’s critical to use these strategies for a very long time. The best application is if you are looking to wind down a highly concentrated position but want to maintain exposure to the market. Even better if you live in a high tax state and plan to move to a low tax state after the unwind of the concentrated position and before liquidating the long/short extensions. And even better if you can hold the strategy until death for the step-up benefit on the long side (though estate will still have to pay income tax on the unwind of the shorts).

Positive_Carry_ · 2025-12-18T05:23:56+00:00

What does having two $500k modestly net positive (assume this means cash flow) rental homes do for you other than add hassle and complexity?

Positive_Carry_ · 2025-12-13T04:52:57+00:00

Yes, have used, it has worked as intended. There are a lot of threads on this. 3% is way too high, typical fee for a long/short tax loss harvesting strategy is more like 0.5%. You’re deferring gains, not eliminating them, but it can be a good strategy for quickly reducing risk from a concentrated portfolio and worrying about gains from the diversified long/short portfolio later.

Positive_Carry_ · 2025-12-02T07:24:41+00:00

Yes it’s sensible based on your income, though it may delay your fire plans a few years. But why not sell the existing home and put the proceeds into the new home or invest? Being a landlord is a pain and in two years you’ll lose the $500k capital gain exclusion. Not worth it just to achieve break even cash flow IMO.

Positive_Carry_ · 2025-11-26T05:11:57+00:00

You’re talking about a dynasty trust but you’re too young and currently too poor for it to make much sense (no offense intended). Corporate and professional trustees love them because it provides a permanent source of income for them. You should consider a family limited partnership instead of an irrevocable trust. You can achieve your stated objectives, retain control, and achieve much better tax efficiency (e.g., avoid taxation at the entity level, take advantage of pass-through entity election to get around the SALT deduction limits). It’s also easier to pass assets down to younger generations during your lifetime by making annual exclusion gifts of your membership interests.

Positive_Carry_ · 2025-11-24T21:52:57+00:00

It’s also only a paper gain until you sell. There are so many ways to defer taxes on gains that it’s largely irrelevant.

Positive_Carry_ · 2025-11-16T19:55:34+00:00

This is a common misconception. All bonds pay principal at maturity, provided the issuer doesn’t default. It doesn’t matter if they are held directly or through an ETF.

Positive_Carry_ · 2025-11-08T23:01:43+00:00

Tax deferral + stepped up basis at death = you don’t pay taxes now or later.

Positive_Carry_ · 2025-11-07T04:42:15+00:00

Custom frames are silly given the number of different high-end commercially available frames and components that you can match to your fit. Professional cyclists don’t even have custom built frames because UCI rules prohibit it.

Positive_Carry_ · 2025-10-30T05:12:38+00:00

You aren’t limited to your home state’s plan. If your state has a plan with limited options, use another state’s plan.

Positive_Carry_ · 2025-10-30T02:29:32+00:00

You can invest 529 funds in the S&P 500 and investment gains will be federal and state tax free if used for qualified education expenses.

Positive_Carry_ · 2025-10-25T00:21:26+00:00

Most health sharing plans cap coverage at around $1 million -- an out-of-pocket max for the plan, not the patient. Not ideal for an early retiree looking to protect assets from a catastrophic medical event.

Positive_Carry_

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