Sold the live-in flip, and the flip part is not what worked
I do fast stuff normally. Buy, fix in ninety days, sell, thin margin, do it again. Two years ago I got tired of paying tax on all of it and bought a house to live in instead. 1,320 square foot two-bed with a bad addition, 248k, 5% down on a conventional loan because I could occupy it. Lived in it with my girlfriend the whole time.
Numbers as they actually landed:
Purchase 248k. Renovation 71k over 22 months, almost all of it out of pocket from flip profits as they came in. New roof, gutted the addition down to studs and rebuilt it as a real third bedroom, kitchen, one bath, all mechanicals except the furnace. I did demo, paint, flooring, trim. Paid out for roof, electrical, HVAC, drywall.
Sold at 431k. Closing costs and commission ran about 26k. So roughly 86k over purchase plus reno plus selling costs.
The thing that made this different from every flip I've done: I wasn't paying two housing payments. On a normal flip I'm carrying the project loan and my own rent at the same time and every week of delay costs me real money. Here the mortgage was just my housing cost. So when the drywall guy vanished for five weeks in month nine, it cost me nothing except living in a house with a plastic sheet where a wall goes.
What nearly broke it was money, not time. Month fourteen I had two flips go sideways at once and I stopped work on my own house for four months because the cash wasn't there. If I'd been on a hard deadline that's a disaster. Here it was just four months of an ugly bathroom.
On the tax side, the two-of-five-years primary residence rule is why I did this at all, and I had a CPA handle the return. Anyone considering it should get their own, because how the exclusion applies to you depends on your specific facts.
What I'd keep: buying something where the ugly part is one contained area. My addition was awful but the rest of the house was livable the whole time. What I'd change is further down the thread, people asked.