I went to University of Windsor as well. (It was my second degree and I was essentially a mature student). It was before the Casino, so things may have changed.
I really enjoyed my time there. The weather was mild and it is a lot easier to get around town there (at least in a car) than in T.O. The cost of housing seemed reasonable. The people are friendly and it is a city that has most of the amenities that you would expect from a major city. It has decent restaurants; Wah Court (dim sum), Sir Cedric's Fish and Chips, Tunnel Bar-B-Q, the Mini (Vietnamese/Asian'/Fusion) were some of our favourites.
To me, being right next to Detroit gave Windsorites a unique advantage of being near (and plugged into) one of the two most important cities in the U.S. midwest (Chicago being the other) but also live in one of the prinicpal cities in Ontario. I had a car while at school, so I spent a lot of time in Detroit; actually, the only time I was really in the City of Detroit was to go to old Tiger Stadium and Joe Louis Arena. Most of my time on the other side of the border were in the Detroit 'burbs. (Some of communities outside of Detroit have the highest per capita income due to the auto industry.) Detroit is also one of the hubs for Northwest Airlines, so I think you would be able to get non-stop, reasonably priced flights for many U.S. (i.e., MCO) and International destinations. If you like professional sports or U.S. college sports, you'll find yourself over the border a lot.
What didn't I like? Well, if you suffer from hayfever, it can be pretty brutal from the end of August into early September. It also gets very humid during the summertime. If you plan on travelling to London, ON or Toronto much during the winter, the 401 highway between London and Windsor is probably the worst stretch of highway on the 401 in terms of accidents and cars ditching. Fortunately, the Windsor station is on the Windsor to Quebec City corrridor for VIA Rail service. So, if the weather is bad, the train is a convenient, hassle-free alternative.