I manage on Oahu in Hawaii and I would assume based on things that I have heard from other hosts and managers in CA that the conversation around regulation would be somewhat similar given that it is a highly desirable destination for both guests and investors in the STR space.Speaking only to what I have experience with here - there seem to be three types of zones that vacation rentals fall into - on one hand you have zones where they are illegal, and while it is possible to run and gun in these areas I don't think the risk is worth the reward if you get caught.

What this rule states is that for the home of purchase to qualify as a secondary home, it must be 65 miles or further from your primary residence or in a “vacation destination”.

(That's a step beyond A-mazing.)David J Dachtera"Success is not a destination.

I would say to only invest overseas if you enjoy the actual travel to that destination.

The Traverse City area has and will continue to be a major vacation destination but not sure about STR opportunities around there.

Almost 100% it is because of one of two reasons: either the door gets broken and the tenant tosses it out rather than letting us know, or they take them off so they can use the closet without the doors (such as a nook office) and then put the door somewhere where it gets ruined (outside is popular, in the rain) or gets nabbed by hobos cruising neighborhoods looking for things to steal. 

I have a particular interest in islands, as my long-term goal is to captain a catamaran and offer tours for snorkeling, sunset cruises, etc.I'm interested in places that offer great ROI without being overly expensive.

I can't imagine Rockford being a destination.

Here’s my situation: I currently own a home the vacation destination New Smyrna Beach, Florida.

Keep in mind that Myrtle Beach is a big destination for Bike Week (Spring and Fall), Youth sporting tournaments year round, golf and conventioneers.