Builders often will put on cheap 3 tab roofs, vs a 30-40 year architectural shingle roof.Also way too many of the newer neighborhoods have HOAs and rental restrictions that prohibit or severly restrict rentals. 

You’ll still need to pay tax on depreciation recapture from the period it was rented.If you sell after March 2026, you’d lose the exclusion and the entire gain would generally be taxable.Oregon doesn’t impose an extra “penalty,” but it does follow federal rules pretty closely—so you’d owe state income tax on any taxable gain that isn’t excluded federally.In short: sell before March 2026 to qualify for the exclusion, and plan for some tax on the depreciation you took while it was a rental.Perfect advice, right on the money! 

you need to read your insurance policy regarding dog breed restrictions.

Some restrictions are pretty easy but they are still necessary or you'll get into legal trouble.

I definitely want to stay clear of anything that could trigger fines or compliance issues, so your point about STR activity in communities with rental caps makes a lot of sense.If the documents don’t spell out any restrictions around owner-occupied MTR/LTR setups, I’ll look into the roommate or owner-occupied lease option you mentioned.

To me, that says that -- no evidence to the contrary -- he rented out in violation of the town ordinance and (my take) now wants to whine that he got caught.AirBnB and other short term rentals (STR) need to be regulated because they impose externalities on neighbors and deprive local governments of revenue and -- depending on circumstances -- pose unfair competition on local hostelries.

@Alex Melara  We managed short term rentals for a while and stopped when the restrictions became to restrictive. 

Quote from @Steven Cingano: It is 7k and I am not financially restricted.

There is a legal difference. if you mess that up, that will get you sued.Third, in the last couple of years, new restrictions have been added in certain states.

I am highly concerned about buying a condo because I've heard Atlanta condo rental restrictions are extremely strict, with many HOAs having rental caps and long waitlists for permits, which would prevent my long-term rental strategy.