City, county, village, HOA can completely ruin or outlaw your business by the stroke of a pen or the vote of disgruntled neighbors. You have a couple of idiots rent your place and treat the residents badly and you're on a list you can never get off of. Increased fees, restrictions, requirements, taxes--- there's just too many ways which are out of your control for your business plan to become unworkable. Once that happens, then the market drops out from under you as a rental investment.

Seems to me many more reliable ways to invest, and the draw of having access to a place in a resort area is of very little interest to me, I want to go to every place, not the same place.