At the bare minimum, you should do the following to make your bookkeeping easier:- Dedicate one checking account and credit card exclusively to real estate.

Sub‑$100K UPB is hard to make pencil once you bake in servicing, reserves, and any legal, so the focus has shifted to roughly $75K-$250K notes where you can still clear around 9-11% yield instead of the 7-9% that felt acceptable in 2023.

The mechanics of the §121 exclusion can work the way you’re describing, but one thing worth thinking about is intent. 

The borrower has been trying to sell the building at steadily decreasing prices; he finally accepted an offer of $1.125,000.  

I'm struggling to see if I'm missing something and to evaluate if I should keep this home and accept a bit of negative cash flow annually as it's offset by the principal paydown and tax benefits of the property, although the return on my equity is very low when compared to just throwing my equity in the stock market or simpler investments, or if I should sell the home and look for better SFHs to invest in, but that leads me to the title; is the market even viable when I'm already cash flow negative with a great rate vs buying new properties with a 3x rate?

That sounds great until you realize that in the core areas (Brickell, Edgewater, Coconut Grove), market rents run $2,800-$3,500 — so no landlord there is accepting vouchers.

I converted a floor of my home to be exclusively an STR in 2025.

A lot of homeowners (and even investors) don’t realize how powerful the primary residence exclusion is.Under Section 121, you may be able to sell your primary residence and exclude up to:$250,000 of gain if you’re single$500,000 of gain if you’re married filing jointlyThat can mean zero federal tax on a huge chunk of profit.The rule is simple: You must have owned and lived in the home for at least 2 of the last 5 years.And here’s the part many investors love: - Those 2 years do NOT have to be consecutive.So if you’re thinking about selling, or you’ve moved around, or you’re strategically planning a future sale, it’s worth understanding how this works before assuming you owe taxes.This is one of the most valuable tax benefits in real estate — and it’s hiding in plain sight.Curious — has anyone here used the Section 121 exclusion before, or are you planning to use it in the future?

Many of these objectives are mutually exclusive, so you have to prioritize.

Your exclusion list will look like the "who's who" of Noah's Ark.