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.

Unfortunately the original setup was not waterproofed very well so we ended up removing the studs from that wall because they were all rotted out.

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

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

Unless I raise it , snow will continue to accumulate, and rot will have again pretty soon.

For example, in early 2021 they let my property manager know that the bathroom floor had a "squishy spot"- but it turns out the floor had completely rotted out and you could see down to the basement from the floor.

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

The block walls were sealed with a product similar to B-Dry, like you would normally find in a basement.

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