I have been to the Cayman Islands plenty of times, and love it, but I want to find somewhere else - a hidden gem maybe... that has yet to explode as a tourist destination, but close enough to a major town that airlines can fly into as I need to make it somewhat affordable and accessible to people who would like to rent it out.

You didn't know who to trust, half of all courses that were on the market were good, tons of fly by nite operators (still many of those), performance in websites was an afterthought... and in general the market had nowhere trustworthy to go to learn how to grow their real estate business using the internet. 

Y son will be attending college soon and I want to be on the same coastal area in case I need to fly to him.

First time landlord and learning on the fly!

Highly recommend flying out and getting to know the area if you go OOS. 

Clearwater definitely enforce their regulations, even if there's been plenty of people flying under the radar. 

I fly back to take a tour of his market meet his wife as well on my dime..

I talked to this guy and he will be flying out here to meet with me in a couple of weeks.

I don't know anything about Toledo but if you're considering that area I would fly out there and get to know the areas really well.

I wouldn't recommend BRRRR in random far away cities unless you're going to fly there and get to know the area really well and develop relationships with a trusted team (key word: trusted).