In the metro area there are some okay hills, but really nothing over 40mph :'( A group of us just went for a sesh this morning and we were hitting high 30's. There were close to a dozen of us, but the Minnesota skate scene is still pretty small. If you made any trips up to the cities (about 150 miles from Onalaska/Lacrosse) I would be happy to introduce you to the other people around, skate as much as possible, and show you runs.
As for winters... yea they're long, cold (compared to Texas), and some times just unpleasant, but they bring snow to the slopes which is always a good time. I don't know if you're a snowboarder or have ever been, but there is a ski area just south of Lacrosse called
Mt. Lacrosse, that I hear is alright. There are also numerous areas around the twin cities and a few on the way up.
PS: Also I'm not sure if you're in to hunting/fishing/hiking ect... but if you are I would be happy to discuss places to go.