If you think of the worst-case and then buy something that works even in the worst-case scenario, you'll be fine.

That being said, as far as making plans for payback, this is sort of the process that my property management company in Connecticut has in place at the moment.

Any earth disturbance over 15,000 sq.ft. requires a full storm water management plan, which usually require some sort of water retention deign, and I believe an O&M agreement with the city. 

I was thinking some sort of rent to own or a Hard Money Lender... who is unrealistically flexible? 

I was thinking some sort of rent to own or a Hard Money Lender... who is unrealistically flexible? 

I would be careful as to where to go in the city to get that sort of return. 

Anyone who thinks this will suddenly kill any sort of vacationing by Americans is crazy.

Here's my question: Would it be possible to sort of work around this limitation and get two separate FHA loans if I live in and hold one FHA mortgage on one property and my wife lives in and holds a separate FHA mortgage on a separate property?

It probably goes without saying, but it depends hugely on the market, and as a rule, the worst run airbnbs will be the quickest to move to LTR (or get sold).  

It's sort of unfair for me to close on it, pay a mortgage and HOA on a place which I can't even move into.