@Trey McGovern Very helpful thread and something I have been thinking about. I knew about lost capital gains taxes but not about self rental rules, which I will have to research. This was a bit of a different situation because there were tenants. I looked at a rural property In Western Massachusetts, just before the pandemic broke out. It had a house and a giant barn with two commercial tenants in it. It turned out there rents were way below market, which was a strike against it, and the back of the barn, where I wanted to put an artist's studio for myself, was in need of renovation. I needed financing. The commercial lender said they would be happy to make the loan but I absolutely must not live on premises. The residential lender said that they would be happy to make me the loan, and it was none of their business if I kept the commercial tenants but to put the rental income on my personal income taxes! It felt messy and I consulted with a real estate lawyer, which cost me $850. Ouch. He said ABSOLUTELY not to mix my own residence with tenants of any kind because of liability issues. I ended up not going forward not only because all of the above, but also because the house needed a lot of work, the barn's issues that were going to bite me in the *** in time, and I found out that it was on the flood plain below an antique dam/mill pond, on a small river that has a history of flooding and washing out bridges and blowing out dams. Ultimately I RAN from it. (The listing agent lied to me about the flood plain.) It was an interesting exercise seriously considering it. I learned a lot. Now I am planning to move to Vermont, rents are high, inventory of houses to buy low, and I am at it again. I'm looking at a $200,000 house with a non-permitted apartment (!) and an inadequate septic. There is also a boundary issue. I would be making a cash offer. At first it looked ridiculous, but I again thought of forming an LLC and renting it to myself, to protect myself from liability from the other tenant. Before I am ready to leave, I could put in a new septic and get the permit for the apartment to be legal. I talked to the town zoning administrator and she said that these always go through. Then I could rent out the house for $2000 plus and the barn apartment is already getting $1200 and is $200 under market rent. Those numbers are great. It is such a complicated property with the encroachment issue (a corner of the barn/apartment is on the neighbors property) that I probably won't move forward on it. It has been on the market for 27 days. It was under contract and their financing fell though, probably because of the encroachment issue. The rule is if the structure has been there 15 years or more (it has) it is likely to qualify for a prescriptive easement. That should be done before it sells again. Mysteriously, Zillow said it sold last September, part of the pandemic exodus from the cities, I am sure. I may hop in the car (three hour drive) and look up the deed and see if it really sold last year. I may throw up my hands and let someone else deal with that mess.