Quote from @Gary Monroe: Personally, I think going for the SF home might be the better bet in the long run.

I bet the first are all cash in 3 days no contingencies.

I am willing to bet this is a violation of air bnb s old policy, probably of any other listing platforms they’re using, and potentially of the law.

Your best bet is to look toward the Midwest markets.

I'm looking for someone concentrated on a small handful of bets where they can truly bring their attention to bear.

House hacking is going to be your best bet.

Expect financing anywhere from 80-90% of Purchase, 100% of rehab (funded in draws), up to 85-90% LTC.Your best bet is getting it in front of a number of lenders efficiently to see who all the 'real players' are for you in this scenario.

2) It took me a while to build my residential  portfolio, and we all know that residential is far safer investment than commercial (especially now); However this is not an office building and related to leisure and "fun".

A judge won't hold them responsible for a long duration lease it they break it but I would bet they will hold you responsible if you try to break it. 

I know it is typically only used for finding vendors when you have an issue but I bet the right handyman would be open to your proactive search.