I will chime in. We moved here 7 years ago and it is the best move we ever made(Islamorada)!
There is no crime to speak of
No traffic and no pollution.
The schools are good.
Local govt for the most part is responsive to your needs
The workers(mechanic,boat car,home repair and landscaping) take pride in their work and give you a fair price.
This does come thru trial and error and after many experiences of people not showing up and just being lazy.
The diving in our backyard is world class! See some of the pix of the divers who live here.
The weather is great even in the hot humid summer(great diving conditions)
People are friendly and generally very helpful.
The bad. if you have to work, high paying jobs are hard to come by unless you travel to Miami.
No big box stores so items are limited.
Housing is expensive, except right now in this rotten economy they are relatively "cheap"
Taxes are very low but insurance is very expensive
Until you find reliable craftsman you will be very frustrated here.
My 2 cents
Wow, I see something completely different
There are 2 or 3 drug raids per week on Stock Island. We have a homeless shelter. Things go missing all the time.
It takes an hour to get out of Key West at rush hour. Granted, we have major construction going on. Islamorada traffic makes me insane with 4 and 5 lanes and a 45 mph speed limit. That's my problem, however.
The schools turn out substandard students. I have 3 friends who teach middle and high school in Marathon, and 4 in Key West. The parents take no responsibility for their kids educations.
The local government is corrupt and make back alley deals constantly. Kick one out, another takes their place. Building permits are granted in offices behind closed doors and the price varies on your ability to carry Franklins.
The workers show up when they want to, sometimes weeks late, sometimes never. They start at 9:30 and knock off at 4:30. Good luck trying to get a weekend craftsman. The Detroit Mechanic (a dying breed) charges $160 per hour. I paid $55 in Houston. I fly my Houston mechanic here, he does a better job. The machine shop charges $120 for a machinist and $110 for a welder. The machinist in Houston was $85. I would have no beef with the welder, except he won't work without a helper. He charges $90.
You have it right about the diving and the weather. It offsets all of the rest.
If you want a high paying job, drive a sprayer truck for the Mosquito control board. They are paid 6 figures. 6 figures.
Not having a Wally World is another bonus as far as I'm concerned.
Again, I've owned houses in Idaho and Houston. The price of housing makes me choke. Maybe I'm naive.
Taxes do seem low. I paid over $5k per year in Houston on a $250k house. The same assessment here would be $900. I can't speak about insurance. Here comes Hurricane Sandy.
In Islamorada there is a Handyman named Louis Martucci. He is a true craftsman, and will paint, make the sliders work, and fix the jalousies. I'll get you his number if you need a handyman, he is awesome.
Still, I would never trade the keys for Houston, or any place else unless I went further south. The prices, taxes and living conditions are inherent to island life. I've lived on lots of islands, and none of them are cheap, in any way.