I know certain areas where I live are limiting those types of permits, etc.

We have a live show tomorrow at 12pm Eastern if you are interested. 

Hi there, I am not located in Chicago, although I did live there for 4 years at one time!

As someone who lives in Dallas proper, and gets good natured annoyed when some one who lives in Plano says they live in "Dallas" they places you mentioned would make folks who live in Prosper blush (40 miles from Dallas) blush.

I live in a rental apartment in a large complex3.

It also makes it harder for other operators down the road--- not your main concern but we all impact each other.What about you and your wife live in the garage unit, and rent out the house for a lot more, at least until all this permitting is figured out.

I'm brand new to real estate investing and currently live overseas in Japan.

To me NO real estate is passive other than your  home you  live in.. 

I live in a rural residential neighborhood that has recently been zoned medium density (townhomes).

Duplexes and multifamily are an option as well, although the dynamics are a little different.If I was still living in BR, I'd househack somewhere in Mid City - capital heights, hundred oaks, poets corner, overpass, etc.