Dang, When attended IU in early 2000s I lived off Grant Street and Smith. I would walk to that Kroger all the time and hang in Seminary Park.
The only homeless I ever saw were at Peoples Park off of Kirkwood. Most were transient and would leave in the winter and come back during the spring and summer. As I recall a lot of them had names and the locals knew them. They were overall friendly and never bothered anyone. I guess things have really changed?