SW WI will be a lot easier during winter than NW WI. That said, it can run the gamut weather wise. Seen it here in So WI get to the mid 70's in early JANUARY and snow in May. Last winter we had a cold snap that hit -10F before windchills. Its not normal, but its possible to get extreme cold even in So WI.
Driving in snow is more of trying to be as smooth as possible on any control input and drive to your ability and comfort level. You'll get to see some rather idiot drivers in snow, especially the 1st real snow fall. Keep your vehicle in good condition mechanically. Keep supplies in your vehicle just in case. I keep an extra set of one of my hunting outfits (can handle well below zero) in the back of my truck along with ski goggles, flashlight, glow sticks, small plastic shovel and a blanket. I know some people who actually keep snow shoes.