Another factor to consider, the main season for tourism seems to be between Memorial day to Labour day, and pretty much dies down completely after that. 

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

My challenge is that its hard to find deals with a strong cash flow in MA due to high property prices and I am not seasoned enough (and brave enough) to start out with an out of state deal or an in-state property that would need major fixing.

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

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.

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.