I expressed disdain at the show when it was announced, mainly for being based on a Twitter gimmick account (yes, really) and for having that samey adult animation style. I finally watched it, and it's surprisingly not bad.
I'm not from Chicago, so take my opinions here with a grain of salt.
Voice Acting - 2/2. You can't go wrong with Lauren Ash. I loved her as Scorpia in She-Ra, and she brings a lot of life to Diane.
Characters - 1/2. Diane is a hard-drinking, partying hedonist with a disheveled lifestyle. When her nephew comes to live with her, the show sets up an arc about learning to care for others. Pretty interesting.
Writing - 1/2. Again, you'll only really appreciate it if you're from Chicago yourself.
Animation - 1/2. Yet another show with the generic adult animation art style. Like with The Harper House, you could make this into a live action sitcom and nothing would change.
Music - 1/2. The rock soundtrack is great, but it's another victim of the lack of a theme song and a generic title card intro.