Please correct me if im wrong.That said it seems the airbnb short term rental business is doing okay (some cash flow?).

That's how people get over-leveraged and into trouble.If you want to invest, do it the old-fashioned way: increase earnings, reduce expenses, save, then invest.

(This will be a business, not a relaxing vacation on the beach.)  

Hypothetical 1031 Exchange question here for one entity with multiple members: If you have an LLC with three people in it holding a rental and all partners decide / agree / vote to sell...

How many will you sleep (more people a little more in monthly utilities).

Not sure how much they make, but something to consider is this question:Once you make the introduction, how can you get repeat business from the flipper (buyer)?

Some people use bank statements, but I am more comfortable using tax statements (e.g. 1099). 

Next time you talk to the renter that's paying late all the time, Maybe mentioned to him or her without getting too involved in their personal life, they should seek out a temporary job a few hours, a couple of days a week until they build up enough to get caught up on the rent, and make a little pool of money to use so they don't get behind again.Some Temporary jobs can be fun, like handing out rubber id bracelets at functions to the participants, or if the person is more blue collar they have jobs for those people too more suited to their tastes. just my 2 cents.

A transaction/title attorney is very diferent from a foreclosure attorney, landord tenant attorney or business structure attorney.

This is far from impossible and many people have a lot of success managing their own STR, but it sounds more involved than what you're looking for.