I was born and raised in Windsor.
Its a borderline hick town, and really, it is just a factory and University town at its heart. The only thing that sustained Windsor for so long was with Ford, GM and Chrysler all having plants based there. Then you have GE factory and Hiram Walker & Sons Distilerry down on the riverside.
The casino's have helped breathe new life back into the cities downtown core and city itself. 10-15 years ago, downtown Ouellette Ave. was becoming a ghost town. I haven't been back in nearly 6-7 years, so I'm not sure what its like lately.
Glen hit most of the negatives on the head.
Its an easy enough city to navigate. The Freedom Festival is kinda fun and the joint fireworks display for the July 1/4th celebration is a fun event.
I'll give you a piece of advice, stay off of Droulliard Ave. at night
