Im in near Bucktown and typically test things out at an empty lot on Wissner or the Buck Town Marina. Im very new too, I picked up a Bixler II from HK in August and have have build several "foamboard" airplanes since (just swapping parts out every time). Ive been using FPV (via fixed wing) for mapping purposes, but there are a few sites where a multi-rotor could be useful. I just finished building a Y6 Multirotor with the APM 2.6 today. Once I get it tuned and get bigger batteries (this thing is a pig for amps)...I'd like to start doing some fully autonomous missions.
I feel ya with the wife in school, me and my wife played school/work tag for the last couple of years and Im glad its over.
Cheers