I have (4) MD properties and have been monitoring JAX and surrounding areas for a few years for investment properties first with a longer term goal as a retirement destination. 

We'll spend a week there at closing to enjoy it some, spruce it up some, and make way for it to make us some money.It's virtually the same exact thing we did with our Destin beachfront condo STR and that has been doing FANTASTIC since mid July.

That to me is nothing but a party flop house, destined to be destroyed.

When it comes to the destin/Walton area, small multifamilies are very hard to come by.

To include Destin area, and as far North as Crestview and Defuniak Springs.

The property is in Pittsburgh after all which is a hot destination. 

I live in a major vacation destination with 2 massive lakes and a world famous fishing river.

The Orlando area is destination that brings in multigenerational travelers, so anything above a 5 bedroom home is desirable within a few miles of Disney and is considered prime real estate for vacation rentals.  

It has peaked my interest and looks to be a growing tourist destination from research I have done.

@Luis PinedaHere's a plug for Phoenix, Arizona that takes into consideration some of the criteria others mentioned above: Here are the four statistics you'll want to consider when researching prospective markets:1) Job Growth2) Population Growth3) Migration4) Housing MarketAnd here are some relevant articles about Phoenix to save you some time:-- Phoenix leads US Counties in Job Growth, New Data Shows-- Phoenix leads the US in Population Growth, New Census Data Shows-- Phoenix is the #1 Migration Destination-- Phoenix is Expected to be Among the Top 5 Housing Markets in 2020I can practically guarantee none of the other markets you're considering are going to be as strong on all factors as the Phoenix metro area is.