Ryan's place was great and very affordable. It was nice to have coffee available each day. I ran into him twice during my stay, and he was hospitable each time. No issues with the shared bathrooms. Never had to wait more than a few minutes and that was really only in the morning. The house is gorgeous, but it is also a giant historic house. So keep in mind that there may be things that are in process of being restored or repaired but nothing was a major issue or took away from the beauty of the home.
Had no issues with the neighborhood having lived in a large city before. Like any city, there are homeless people, which can be off putting (especially to people not used to city life) but is a reality. I didn't take the train at night (which I avoid in any city) so can't speak to that, but it was easy and quick to get around using the L.
I would definitely recommend staying here and would stay again myself if in Chicago again.