Bob's place was exactly as advertised! The apartment was a great size and in a great neighborhood, and Bob was super communicative. I hope it's available the next time I visit Chicago, because I would 100% stay again.
*Accessibility point: the steps down to the apartment (it's basement level) are steep, and I wouldn't recommend them for someone with mobility issues. However, I believe there's a way to enter through the back that wouldn't involve stairs, but I would confirm this before booking if you have any mobility problems!