Biggest issue to me would be water intrusion/mildew and the accompanying smell.

Personally, I do not believe all the concerns about a bubble, and comparing today's market to 2008.

He has several Civil and Criminal records that concerned us. 

(I've flipped 3 houses at the time of writing, all went well, no late payments)So the question is, what are other investors seeing as far as rates are concerned?

the solution is better tenant screening. do it yourself if you don't believe your property manager can do it 100% to your satisfaction. either you or your property mgr should meet the lead paint tester and accompany them to the rental properties with copy of the keys to let them in. put your tenants on notice ahead of time. if you don't have a license to rent then you can't rent and that means automatic eviction, imho. make it clear to your tenants.

I Have no idea how to factor in above concern of housing market dip and how long that could take to recover from, as well as the potential future rental market if I decided to rent instead of sell.

If your bank is saying they can give you a loan then what exactly is your concern?

Other buildings in the area have HOA costs that are around $500+.I Have no idea how to factor in above concern of housing market dip and how long that could take to recover from, as well as the potential future rental market if I decided to rent instead of sell.Felt like my post was disjointed, but figured I’d post and add detail later.

My concern is if whoever he finds as a housemate doesn't qualify on his on and can't get a co-signer.

Other buildings in the area have HOA costs that are around $500+.I Have no idea how to factor in above concern of housing market dip and how long that could take to recover from, as well as the potential future rental market if I decided to rent instead of sell.Felt like my post was disjointed, but figured I’d post and add detail later.