This would pay us back less than we were owed but still enough to come out whole.We all tried to negotiate a short payoff with the second-position lender, who foolishly demanded payment in full.

If you find something that works well as a short-term rental, but doesn't work well for you as a home, you'll have money but be dissatisfied when you live there.You don't even need it to produce a profit.

I would consider the returns you have now - then run a different scenario where you put that money in a basic S&P 500 tracker.

As others have mentioned, you typically need some liquid capital to get a deal done even if a hard money lender was funding 100% of the deal for you. 

I usually just google "market name" airbnb or short term regulations.

Even if it was a short term rental before, it'll only take one neighbor to complain to cause you trouble.

First off, thank you for your service, and congrats on transitioning into teaching—what an awesome way to continue making an impact.My wife, Kelly, and I are in Volusia County, where we run a real estate brokerage and property management company.

Even if they do 85/15 your going to have to leave money in it.  

DSCR is not low money down or low money into a deal.

Use the money only to stabilize assets and yourself.