I lived in Madison way back in 1982 after graduating from A&M. Obviously, this is very dated, but I suspect much of it holds true today.
Madison is the Austin of Wisconsin. Very liberal, but also, a really neat town. University of Wisconsin is there as is the State Capitol. In fact, the Capitol building sits on an Isthmus which separates Lake Mendota from Lake Monona. Great place to live if you like the outdoors.
State Street, which connects the Capitol to the University of Wisconsin is pretty neat, lots of shops/restaurants/etc.
Winter is bitter cold, but the locals embrace it and do their thing...bowling, ice fishing, hockey, and drinking beer and brandy. Lots of drinking. Bars seem to located on every block of that city.
UW Football is a lot of fun. Camp Randall stadium holds about 80,000 people and was packed when I lived there even though the program wasn't nearly as developed as it is today. In my opinion though, going to a UW hockey game was even better. In a way, getting a ticket to a hockey game wasn't always easy as they sold out all their games (several members of the 1980's Miracle on Ice team had Wisconsin connections, including the coach Herb Brooks).
The management of Kraft-Heinz did a dis-service to Madison when they completely shut down the corporate office of Oscar Mayer a few years ago, which is why I was there. The city has moved on, but that was a sad day for me when they announced they were executing a cost saving measure and moving to Chicago.
If I had to sum it up, I'd encourage him to go...I enjoyed my time while I was there.