I already purchased a property in Winter Garden few months ago, bordering Windermere and am very happy with it so far.

Hi Easton,If your Goal is to maximize the rental income, based on all the rentals we manage some of the best areas I would recommend would be Winter Garden, Windermere, Oviedo, Clermont, Lake Nona, Altamonte Springs, Winter park, Colonial Town and Apopka. your welcome to reach out for free rental analysis if you find some properties you like.

A lot of 2/3 flats in Chicago have non-conforming garden units.

A community garden? 

If you like gardening, become a landscaper, etc.  

There is College Park, Winter Park, Winter Springs, Winter Garden, Oveido, Ocoee, Apopka, Conway, Belle Isle, Pine Hills, Richmond Heights, Dr.

So in your example being in Houston, this would be like rather than being fully paid off with a Garden Oaks investment house, you're putting 60% down on two heights houses + $15-20k of reno in each.

I don't know much about the SW side down closer to the Airport (Mars Hill/Drexel Gardens) or the NW side heading towards Lawrence (Brightwood/Devington).

Not your garden variety, Im talking black, orange, with furry mushrooms.

Also, the proximity to Busch gardens makes it very attractive for your next tenant.