If I go to a bike shop in South Bend, I will probably have to spend a lot more than $200 right?
Should I invest a lot of money in a bike that will be ridden through snow/tough weather?

I'm actually in Southern California until mid-August, so Craigslist would have a lot more options around here, but shipping a bike would be another $60-$80, so i'm not sure if it's worth it.

I also don't know anything about bikes, and can't tell between a good and a bad one, so Craigslist wouldn't be a good idea, unless I have someone help me.

When choosing a bike, should i primarily look at brands? Are there certain brands I should stick to (ie. Hardrock) to ensure I get a quality bike?

Jon: the Schwinn bike you recommended looks great, but I'm too short for 26".