You can get a good, high-paying job out of UM, you just have to remember that that job is going to be in Miami, which in most people's mind, isn't a bad thing, but it depends on if you want to live in Miami. From Madison, though, you'll be stuck in the Midwest, and while that encompasses a wider geographic area, do you really want to live in Milwaukee, St. Louis, or Chicago? That's the question you have to ask yourself. They are both pretty good schools, and at Madison you will have a better chance of being able to practice outside of the Midwest, but you should go into them realizing that, chances are, as a UM graduate you will live in Florida and as a UW graduate you will live in Wisconsin or Illinois.