Need some advice on buying two properties

I am a first time home buyer looking to possibly purchase two properties. One would be in my hometown and a rental or potential future full time property in Kissimmee Florida. I’m undecided about if I’d move to Florida full-time, it depends on if family would come too. Is it smarter to buy a house here and condo there or vice versa (house in FL, condo in CT)? I figured I could probably rent anything I don’t buy as it’s near Disney and would get some rentals but it’s main purpose is for vacations. I have the money to buy a condo outright so I’d have one paid for and one mortgage. What would you do in this situation?