cyphire– I don’t know about the financial aspects of your choice, but FWIW I think for lifestyle Madison is fantastic. I’ve lived in plenty of places (NYC, Buffalo, LA, DC, SF, Atlanta, and Tucson) and visited most of the 50 states, and except for hard winters, Madison really is quite a nice place–though I expect you already know that or you wouldn’t be moving. It is one of the few places in “flyover” country where I would like to live.
The university is also great and it’s reputation is on the rise and the convention center there is one of nicest I’ve visited–and I’ve visited some pretty nice ones. It’s a Frank Loyd Wright design, called Monona Terrace I think. Madison is truly a wonder to bi-coastal snobs, such as I myself. ;^)