So it's not likely the fiduciaries would gamble on an assignable contract.

Buying real estate in California or any other high-priced market is more like gambling than investing.

Yes, sales prices in the FL market overall have increased recently - but betting on appreciation is a gamble.

If you can but there are a few arrangements thats need then sure.But NEVER invest with "need" money PERIOD, because then you blur the line between investing and gambling.

However, this is a gamble and we have put some nice upgrades on the house that might have to be redone before selling again

Maybe others that have gone through this can speak more to it but if it is with the City of Portland then expect that to be a pain and to cost a lot with the gamble that they don't approve it.4.

IMHO the easiest and most definitive is for the owner and you get an authentic survey. 

Typically expectations for NPNs by newbies is unrealistic and what they think they are investing looks more like gambling.  

I feel like I'd be taking a gamble with it.

Remember, people use Airbnb for not only a cheaper visit, but also a more authentic one.