Define "successful." If this fellow wants to be a 14:20 guy instead of a 14:50 guy (that's if going to say UWL over UWM will ACTUALLY do that), then good, go for it. But if he wants to go to school at UWM and get an athletic scholarship, how can you blame him?
And I'm familiar with the general culture/student life of several of the UW schools--Milwaukee, Madison, Stevens Point, La Crosse. As if one is SOOOOO much better than the other? Give me a break. It's Wisconsin all around and I'd argue that he would get a better experience at Milwaukee (I was there for graduate school as well) against some podunk college like Stevens Point (I finished my BA there). I love them both.