I've been through lots of tenants but nothing too horrible out of pure malice.

It really depends on how you're defining "best".From a pure cash flow perspective I'm sure you could do the best in small, rural towns in the south. 

@Rick SantasiereThis is purely a question of how comfortable you are with risk.  

I like real estate more purely because of the leverage and ability to control what you own.

I guess my point is, deal has to make sense from pure analysis point, but I don't hate on guys just trying to hustle and make a buck doing whatever they can.

If you buy because you want to own there as opposed to being a pure investor, you can care less about the state of the market and take advantage of a bargain if you find any.Or maybe, you prefer to wait that the tourism and market fully recover and pay top dollar?

Ultimately, it seems like it is purely up to me whether I would like to build a relationship with anyone in the group and whether I will get anything worthwhile out of the group based on what I put into the connections present in the group. 

Airbnb s security deposit is pure BS.

You would definitely want to consult an attorney or CPA (or both) in the state where the properties are located for a better understanding but from a purely tax perspective, any state that imposes income taxes most likely would require you to report the income from a property in the state they operate in on an accompanying tax return. 

This would be purely investment and therefore I need to do a conventional loan and downpayment.