This sort of thing will never be able to be handled through a rigid software accounting system. 

What one person thinks is remodeled and nice is a 3 star stay for others.Sometimes it is a big thing like a dirty house etc or sometimes it is a bunch of smaller things like 3 forks, no bowls, poor quality linens, that sort of thing.My charity booked a large STR for a 2 day board retreat a few years ago.

Things change rapidly so double check that info, I have not focused on Lease Options for a while now so I'm sort of out of the loop as far as the lenders flexibility at the moment.

Before I bought this, I was open to buying a large house and doing the roommate thing, as a sort of house hack.

I understand this sort of advice comes with disclaimers, though hoping someone can just share from their experience.

My gut feeling only is that these are some sort of business improvement/development loans -- run by a county corporation  the "LID") and that the monies are not being paid back.

too many  variables to provide any sort of beneficial answer 

Account Closed Sort of depends on your definition of wealthy.  

What sort of catalysts or measurements are we using to know when to off load our flips or homes financed with short-term money?

Need help sorting out all the pros and cons, tax and financial implications, etc. given the current market.