The Poconos Association of Vacation Rental Owners put out an impact study that talks about the big picture which is good.  30 million visitors coming each year, nice things to do, mix of resorts and outdoor destinations that are not overcrowded, a pleasant place to drive to. 

Full time happens with 100+ units and often you see people scale a business on the side, like PM, construction or something unrelated like a resort in Costa Rica ;-) I am no different - I "retired" from my corporate career in 2015 and quickly realized that I can only watch so much daytime TV. 

From Florida's largest insurer - as well as the one of last resort, Citizens Property Insurance:  "When a roof replacement is required, and a coating or sealant is used in lieu of roof replacement, the risk remains ineligible for coverage." 

Like @Michael Baum and @John Underwood said, this is a highly competitive area and I don't typically recommend going into a neighborhood that isnt a resort.

The package includes:- 3 nights at a 5-star, all-inclusive resort - All food and drink- Access to 3 keynotes and 60+ speakers and breakout sessions and guided networking - 3 evening events - Networking breakfast x2 and Networking lunch x2- Access to the exhibit hall, and more! 

Outside of real estate, I enjoy skiing in wintertime, basketball all other times and having fun with friends and family all aboard this crazy ride. 

Your state has a market of last resort called the Indianna FAIR plan that may  write it.  

One was just acquired, the other is top of its market in a resort town.

I have a STR house in a resort town, but the city’s new stricter policies have really cut into my revenue.

Unlike your rental, my rental is in Orlando in a gated resort, so there are less outdoor space but lots of community facilities.