So to help cover expenses and see some cash flow would focus on multi-unit property. 

Florida did just have back to back hurricanes but a proper master insurance policy and coverage usually covers that type or perilYou are facing a declining cash flow situation which is due to the HOA fee's so while there is still a profit and you have equity sell and look for a 2-4 units.

It's especially frustrating considering that I'm living in the unit below.

Currently, I own 26 doors and run a property management company that oversees 350+ units.

Unfortunately it's not practical in a rental unit.

When I used the Insight Property tool on BP it had the median rent at $2500 per unit. 

Health professionals are generally looking for 1-2 bedrooms and even travelers in other professions look for that size unit.

I have a unit that is paying significantly below market rent.

Ask how many units they manage and how much experience they have.

I dont know how many units you are talking about, my biggest problem was tenants having easy access to me.I finally decided to use a software and got an internal property manager so moved away from it.Currently setting up the maintenance request portion of it, so will see how it goes.