Managing these will be a breeze.

Based on rent of $1500-1600 and mortgage payment of $1700-1800 which doesn’t even include maintenance, management or capex it doesn’t seem to make any sense to keep it as a rental.

Fireplaces can add to the value of your rental if they are well maintained and managed.

I’ve experienced success in the STR market here in St Pete myself but I’ve since transitioned my properties to long term rentals for convenience and time management sake.

I have a C-Corp (no assets) as the Prop Manager  to manage leasing and rental collection for all 4 LTRs.

Roof, HVAC, sewer, etc.Has the property been poorly managed?

Do you focus on brokers, property managers, or other investors first?

They subtlety put the burden of proof on me to show that my line is capped so my contractor continues to install cleanouts so we can flush and scope- cleanout has to be put on the Water Districts vacant property. 

Corporations and large property managers are the future, and the hoops you need to jump thru are necessary because of too much legislation.

As for property management software, options like Hostaway or Lodgify can streamline bookings and communication.