Many areas have worked hard to shut down the short term rental business.

Those costs to both shut down the biz to upgrade/replace and the cost of doing the work are huge capital costs. 

I wouldn't go into something already knowing it was illegal, you are just asking for trouble.Just because other people are getting away with it currently doesn't mean they won't get shut down in the near future.

Golf cart license are being restricted due to to many people, sinking foundations- either to close to unrestored sea walls or not enough pilings or fill dirt not allowed to compact, off grid experience, check on sewer and water infrastructure- when the water pump went out, the island shut down, the islands systems are being overloaded, what type of experience and thus rental rates are you shooting for?  

Buy at the local restaurants, use peoples names, tip well. 

The closer you are to the beaches and to the restaurants the better.The regulations are friendly.

We were using a local small company that did exactly what evolve does in PA then they got shut down by the PA real estate regime.

In addition to being near the street car, we were surrounded by historic buildings such as the Anne Rice Estate House and a variety of the city's highest ranked restaurants that are regularly featured on travel channels such as Shaya.

, cleaned, and installed new HVAC, ran all new pex lines/valves/shut offs, all new hardwood flooring and carpet, all new and expanded kitchen cabinets, new appliances, created full bath and connected it to a bedroom to create en suite, repurposed 2 unused rooms (1 into a 4th bedroom/office/playroom and one into a family room, installed new interior and exterior lighting throughout, new automatic garage door, and landscaped.

Created en suite bed/bath, extra bedroom/office/playroom, created family/tv room, added a couple of windows in dark rooms, installed new HVAC, ran all new pex lines/valves/shut offs, all new hardwood flooring and carpet, all new and expanded kitchen cabinets, new appliances, converted 1/2 bath into full bath, repurposed 2 unused rooms (1 into a 4th bedroom/office/playroom and one into a family room, installed new interior and exterior lighting, new electric garage door w/remote, and landscaping What was the outcome?