Pittsburgh and Madison are both low COL cities with great engineering schools where only a small handful of companies are soaking up all the talent. Definitely underrated.
To be honest, both suck compared to NYC and SF. There's just no comparison. NYC and SF have high numbers of PhD level tech talent, neither Pittsburgh nor Madison have anywhere near the number of the MIT-Stanford-Caltech PhD crowd. NYC and SF have higher density. And NYC, for example, has far more jobs in industries unrelated to tech. Not only more jobs in other industries, but way more other industries in general. Which is always attractive for the significant other.
The name of the game is to get high end tech talent. So sure, the University of Wisconsin can crank out code monkees for you. That's fine if that's all you need. But all the PhDs from the elite tech schools will sit down with their spouses or significant others to think about where to live and Madison and Pittsburgh just won't be terribly high on those lists. It's not all about the PhD that Google wants to hire, you have to have something for his or her spouse too. It's a lot easier to do that in NYC or SF. Just kind of the reality right now.
Don't know about CS graduates per se, but Madison has the reputation of being a place where people come to attend school, and then don't want to leave. I don't want to leave here either. ;-)
You guys drink/ booze like it's going out of fashion. Must be all those cold long Wisconsin winters. Madison is an OK place in summer, but not a place I would like to live in. And this coming from a guy who grew up in Michigan. I prefer Ann Arbor for that reason.
Wisc-Madison has a great reputation for mech/industrial/ops types of degrees.
I'm waiting for Minneapolis to get that break. It's happening.. the big techies are coming (Amazon is here), as well as a lot of home grown tech. I think the new 2040 plan will drive a lot of tech growth.