Hey Dave,
Come on back!
Can't say I'm real familiar with areas SW of Madison, but New Glarus is an interesting town if you like a bit of Old World atmosphere. I know people that live in Belleville that like the town, and my wife's family lived in Monroe at one point.
Not sure about work in that area though, depending on what you plan to do.
I grew up in Madison and lived in the Chicago suburbs for 20 years, moving back to this area about 5 years ago. I wish I had more time to ride, but I'm right on the edge of city/country so it only takes a minute to be on the backroads.
Housing in that area will sure be quite a bit less expensive than what you are used to, that's for sure.
Best of luck.
Jay