Short-Term Vacation Rentals under 100k?

[Brandt Tingen]

I am looking to buy a vacation property, but I would like to start off small and get a place for less than 100k to start.  Oh yeah, I'd also like the property to throw off a little net cash per year, and be in an area where short-term rentals are not frowned upon.  I have been looking at a few markets across the US, and am beginning researching the Caribbean, and Central America.  Am I crazy?