So, if an appraiser decided to use those, they should adjust downward for the 3rd unit and calculate a time trend adjustment for the older sale.

Make sure to comp out rents and figure out the summer season, screen tenants, etc.

Nice big level lot for this older home built in 1980.

Jorge, I love Florida RE as much as anyone, but I would not count on insurance premiums decreasing, let's just try to get through hurricane season unscathed.

Condition of Properties: It's understandable to feel hesitant about purchasing older multi-family homes that need a lot of work.

Just get a firm exit strategy in place (and a backup) for financing before you take action - most cashout refi products have seasoning requirements these days. 

Welcome to BP Jarrod,These forums are a great place to learn and meet people, whether you're just starting out or you're a seasoned investor.

Airbnb/VRBO will not take the guest side as they are booking a home in an area prone Hurricanes during Hurricane Season. 

So, this skips the need for a cash out refi (saving that cost and avoids seasoning issues) 

Just make sure you know how your going to setup your take-out/permanent financing before you start this process as cashout refi's for conventional have seasoning requirements now and delayed financing has rules and timelines as well.