This is a vacation destination and we really only have 3 busy months during the summer. 

And it’s an easy destination to market towards (a Zillow link for the property posted on Facebook, email, text, etc) people tend to remember Zillow easier than property managers website.

From an investment standpoint, the town of Telluride has put in a concerted effort to make it both a summer and winter destination with 2 world renowned film festivals in addition to bluegrass, jazz, blues and brews, wine and car lovers festivals filling up the summer calendar. 

I can't speak to the Naples area but I know that Destin is one of the best short term markets in the country per a number of market reports I've read. 

I'm thinking of buying a Condo in a fairly popular tourist destination a couple blocks off the beach in Hawaii.

Unless you're destined to open up your own PM business, you are almost certainly going to want to hire one eventually. 

It's a huge white space that nobody is taking advantage of and it makes sense produce content that people want to see, now you will start getting recognized as Cody the real estate agent that helped me make the decision to move here and why would they go to anybody else to help them find a home if then the person that help them make that decision.Conclusion To sum it up, you will be a media company/ real estate agent. you are going to be the content producer of information that buyers and sellers wantlike writing reviews of the best restaurants, interviews principles on why their school is the best, going to every destination there is to go to and provide walkthrough videos, etc...If you approach it like this then your now the source that people who are looking to buy in your area and sell are now going to go to. 

Destin has some larger vacation homes, but in my humble opinion the prices are already toward top levels. 

The location being a high year round vacation destination helps keep occupancy full year round.

Again, this is in our markets which are year round destinations.