@Ellie Narie your best bet is to talk to a Qualified Intermediary, they act as escrow for a 1031 exchange.

If I was confident one way or another I would place my investing "bets" accordingly, but for now I make decisions based on where the data and trends suggest the most reliable chance of producing a return. 

I ultimately settled on Columbus as my target market and haven't had any regrets as the years have progressed.

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.

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.

Less affluent areas that will benefit greatly from occupancy taxes and tourism may be a better bet.

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.