I'm moving to Florida, been there a few times over this year house hunting and planning to settle in Winter Garden.  

Quote from @Brandon Moss: Quote from @Lawrence Briggs: I have officially CLOSED on my SECOND PROPERTY—a single family home, investment rental.

I am planning to move to Central Florida first part of next year, probably around Winter Garden area.

When I see a basic garden variety home in a mid~line community in OC, Ca., go for one million dollars, I think, man, how many units can I buy with that million!!!  

I'm not sure what the current statutes on vacation rentals are, but the Colliseum hosts large concerts on a fairly regular basis so if you wanted to go that route you could get a house and vacation rental it in the Spring Garden/Chapman area.

Moss Woods PLLC is great.

I currently own a duplex with a garden unit(typical Chicago brick style) in Irving Park.  

century 21 Castelli in Garden city.  

There's not just taxes and repairs but also insurance, vacancy, water/gas/electric/internet, garden and maybe putting something aside for once-in-a-lifetime big overhauls (roof for example) every month. 

Some others that I don't know the legality of in any given area but that you might look into would be parking spaces or urban farming/ gardening, in non-covid times you might be able to lease the land in exchange for a share of the profits from whatever crops are grown and sold at a farmers market.