In the scenario that airbnb dries a little I can simply do long term rental and not have to come out of pocket on the Orlando properties. 

The ideal climate is dry with few weather extremes.5.

Then, once you figure out a plan with your lender, it's up to you to convince your basketball team of a family to follow your hair-brained idea.

that is where i'm having the  most trouble since they are in the same zip code but to different part of the zipcodeThe only one that I see that is on the same side is 3143 Riverside Dr. I

Maybe make sure to add a pest and dry rot inspection, scope the sewer line and maybe check for radon.

When I get to them, the home owner might think of me as his "fair-haired boy" and want to talk to me.

Did they require a lot of rehab (roof, siding, foundation work, serious dry rot, water damage, etc.) or was it mostly cosmetic clean up? 

I think the money has to dry up for this cycle to stop, OR we slowly (painfully?)

They rent well the value dynamics are different thean dry front properties of course and the factors that @Wayne Brooks mention are important. 

Dry rot in floor joists, rafters, other structural members."