My family has had season tickets in section H for 55 years.
For most of the last 20 years I've lived outside of WI, so I'm lucky if I get to one game a year. Thus the novelty is still there for me and I enjoy going to the games, win or lose. It's the totality of the experience - going back to Madison, walking with the crowd to the game, going to a bar on Regent or Brats before the game, hitting the bookstore and State Street before or after the game, dinner up by the square afterwards. For me, it's about much more than the game. Maybe if I went five times a year I might feel differently.
Just curious, other than winning, what would make you feel differently? Now that it's legal to pay players, and they're in a conference with much deeper pockets in Oregon, Michigan, Ohio State, and Penn State, they're very unlikely to finish in the top four and go to the conference championship game and/or the Rose Bowl. Barring a ridiculously easy schedule fluke I think that 9-3 is the best they are going to be moving forward regardless of who is the coach.