Although most of my stays are <7 days, I've had a few longer stays (business travelers and a family that was going through a full home remodel).

Would love feedback from anyone with personal investing and/or property management experience in these cities.

Personally, I wouldn't offer SubTo or a Wrap, For reasons I've written about fairly extensively. https://www.biggerpockets.com/forums/70/topics/1227199-the-m...However, I would sell on "Lease Option" and that may work for you.

Also, do you have enough personal income coming in to cover the negative cash-flow that this deal will have along with the unexpected expenses that may come up? 

There are very few lenders that will allow you to close in a personal name in FL.

DSCR will help if you are tapped out of conventional loans and you don't qualify for a traditional loan based on your personal DTI.

The person in the response above who got crushed by a $5000 repair never did have $100-200/mo. cashflow.

I have no personal experience with them but they are the only company I know of that are built more for self managers and small portfolios. 

However, I have found local property managers to be very helpful in stating whether an area was difficult to rent, what the market rents were, and even personally knowing some of the tenants of buildings I was considering.

Excess depreciation could be suspended as a passive loss unless you qualify as a Real Estate Professional (REPS) or materially participate in a Short-Term Rental (STR)—which would allow you to use the additional depreciation to offset W-2 or business income.