A lot of college kids around here like to ride around on beach cruisers. Ive seen one or two decked out with panniers. Most all of them have some sort of front basket. There are hills here but nothing too major. I don't know how severe your hills are there. Ive seen some with a geared hub so that could help with hills.
I liked wearing vans, but they always fell apart very quickly when riding bmx. Also I remember them not gripping all that well. I used to wear DVS and DC quite a bit. I remember them being good shoes for riding. Converse are very good for riding in, but grippy pedals are a must. They are a bit slick. Also the damn felt on the bottom always comes loose after riding a while.
If your trying to save on a pack, and want to keep using your hiking pack you can try rolling up the straps and holding em in place with rubber bands or hair ties. If your in college and going to be carrying books and a laptop, invest in a decent bag with a computer pouch. My pack doesn't have a computer pouch. This makes it very sketchy biking with my laptop.
My two cents. Hope some of it helps.