The property isn't 'cash flowing' but our renters downstairs take $2,100 off our $5,700 mortgage so that comes down to my fiance and I paying $1,800 to live here.

Cash flow is helpful because it ensures the property pays for itself and is a safe investment.

If the deal is right you can use hard/ private money to finance the home purchase and some or all of the repairs, then do a cash out refinance to pay off your hard/private money. 

The price you pay for being part of the Disney World spoon-feed of guests is that the barrier to entry for profitable STRs (ones that leverage close to or max LTV) is very, very high.  

It's amazing how cheap it can get when you're paying physical cash and having your contractor pick it up at the warehouse.

In the “old” days, people would have the seller pay the lender so as to not “alert” the lender that a property sale had taken place, so that the lender def wouldn’t trigger the so called “due on sale” that’s a part of almost every mortgage or deed of trust document.  

They pay for it. 

It takes a couple of calls to schedule, then they pay the invoice.

I would also share pros and cons of paying taxes on the windfall versus owner carry.

You will get some of these as well (This inquiry was for one of my 1500 SF 2 Bed + home office units)..... but by no means does this investment strategy warrant paying for a course.