A financial planner, CPA, and others may be better resources for you in deciding which is the best play here based on the immediate health needs and life expectancy.Hope this helps. 

But proximity plays a role to.

@Seth KristianNot an attorney but fractional reserve lending has been challenged in the past as have mortgagesIn most cases unjust enrichment can come into play when it’s disputed but if you did not receive the $, you cannot say you don’t owe it back.If you want a crazier case read greenleaf case in MaineThat one is actually case law (this one Daly had it overturned).Free homes in Maine forMany if they knew about it.

Decide which game you want to play.

@Jeremy H. you seem to think that short term vacation rentals are a RE play when they are in fact a business.

Thats way to skinny a deal playing with those numbers 

I'm just playing the devil's advocate.

But now he is staying so we decided to play the cat card, and told him that per his lease pets not allowed and if he would like to keep it we will need to amend his lease to include additional $100 pet rent plus collect additional security deposit.

That’s all rhetorical of course, but what role is Airbnb playing in all this?

What's the play here?