And even then, why would you accept to block your calendar between the time they book and the time you receive payment by check, and the risk of cancellation and the pain for managing all that?

He purchased it for 185k, so he's probably only looking at around 5k in taxable gains.CAVEATS:  1. if he was renting part of it and took depreciation costs on his taxes, there'd be depreciation recapture2. if he didn't claim it as a primary residence, that might be hard to change retroactively to get the exemption 3. if he can prove renovation expenses, that increases his cost basis and can provide extra cushion there.If something in there is messed up like say he claimed residence at a family member's house and can't take the 250k exemption, you could talk to him about owner finance to spread the gains over a few years to be less painful.

I have turned many people away including someone who wanted it for work x 8 month which was somewhat painful.  

If you're in a fast-foreclose state, like Georgia or Texas, this should be less of a worry, but it could be a MAJOR pain if the deal is in, say, California or New York.Whatever the seller's concerns, there are ways to address them: You just need to have a frank and blunt conversation with them, ASAP!

So we are really trying to minimize the pain this time by getting as much info as possible.We are looking for income in retirement. 

Plus there the capital gains idea (unless you do a 1031 exchange, but that can be a huge pain).

The HOA's can be a pain but depending on the rental restrictions, a great home in a nice community, preferably west of Rt 41, near beaches, could be a winner.

For some its a pain. 

May also want to mention you have a jealous relative that's making trouble for you but whatever it takes, with their assistance, you'll correct any property issues.While this may be painful from a financial perspective, don't give up now.

@Brent FisherHi Brent, I am a father of two and feel your pain.