The JMLS scholarship is dependent on remaining in the top third of my class. I figure, 18K/year tuition, plus about 12-15K/year in living expenses leaves me with around 90K in debt after three years.
You should find a JMLS student and determine if they do anything funky like place all students on scholarships in the same section, which would lower your chances of keeping the scholarship.
That said, I would think that Wisconsin has a much better reputation than JMLS. From talking to people in Chicago, JMLS is widely considered to be worse than Loyola/Depaul/Kent. So you'd be competing for jobs against grads of five different schools that people think more highly of than JMLS (counting UofC and NW). Sounds like an uphill battle, depending on what type of job you would like to do upon graduation.