I generally recommend if you're not going to buy a property in the city/market where you currently live, the next best place to look is where you have family (and presumably a place that you'll visit relatively often and easily).What is your price point and are you looking for turn-key properties or something along the lines of a "fixer upper", assuming you buy in Peoria or a similar priced Midwest market?

Looking to purchase a duplex, triplex or fourplex in Panama City and do short term rentals for summer months and long term through the winter. 

There are certainly value-added opportunities in the city.

Quote from @Makani Donaldson: From what I understand, different islands or cities have different rules, and they are getting stricter.

I’d recommend listening to the straight up Chicago investor podcast for local information, going to the variety of meetups that are in this great city, and meeting a lot of the people posting here. 

The tricky part will be to get the the city to change your property's zoning to multi family (if it isn't already).

I have a client in Kansas City that does this.

I don't know CLE per se (I'm based in STL), but I know the financial side of gut rehabs in urban centers of big cities.

I am moving from Kansas City Missouri.

Then later on purchase homes with cash (single family homes), I would like to learn how to read the market and know where a state or city is thriving but also learn where it's not.