I don't think it's arguable that Wisconsin has had more success than Minnesota, however you choose to define it. Minnesota would take the last 25 years of Wisconsin in a heartbeat.
Of course you're right about really any other bottom feeder, but that's all contingent on them getting their [Mark May] together in football, which they seem to be incapable (Minnesota/Illinois) or uninterested (Indiana/Purdue) in doing (which is why they're the bottom feeders to begin with).
Mason was the closest, but he wasn't really that close. Holtz maybe could have been, but he bolted after 2 years for ND. But, back to the original premise and to your first point: Wisconsin isn't having outrageous success year after year. They're not playing for national titles. They're competing for Big Ten titles and the occasional BCS/NY6 bowl. That's what Minnesota should aspire to and I don't think it's completely out of reach. They just have to quit with the fuckery.
On the topic, I'm not exceptionally well versed in Minnesota history, is there a reason the program careened off a cliff in the 60's?