IMO, Madison is a little overrated. I grew up by the Twin Cities area, went to college in Madison, lived in Ann Arbor, Houston, and a couple of other cities. I've been in all four regions in this country. For the size of Madison, the city offers a decent amount of stuff. What I liked about Madison was the good amount of places to eat (don't have to deal with the, "we eat here 100 times in the last year" stuff like you do with the really rural areas in Wisconsin), very little traffic, and college sporting events. Outside of that, I didn't care for Madison at all. One thing that Madison does have going for itself is the healthcare. You have three good sized hospitals in a central area. As far as how the city is layed out, I hate it!
In the state of Wisconsin, the only city I would want to live in is Madison. I don't care for the freeway system of Milwaukee.
Chicago is the only major party city in the Midwest. When you want to impress a lady, you take her to Chicago. As far as myself wanting to live in Chicago, I'm sick of the cold! Oh, winter in Madison can really suck as it can get really, really cold.
When I was in Ann Arbor, MI, I was bored off my ass. I don't find anything in the whole state of Michigan interesting.
I enjoyed Houston a lot as I enjoy warm weather. Most people would hate to be in Missouri, but I enjoyed my time in Missoui as it offers what I would like.....cheap living, warm weather, etc. I've been to Boston and don't want anything to do with that city. I"ve been to the University of North Carolina area and I enjoyed my time there...I like that area. Myself personally, I prefer the warm climates. I don't get any mor eenjoyment than being able to read my medical school material in a warm outside in the nice sun by the beach (Bradenton, FL is where I go to medical school)......I came across this thread randomly when doing a Google search and just wanted to provide my own insight.