I'm currently attending UW-Madison as a first-year PhD student. Many of the other students that have came in as unfunded (and wanting to just do Masters) have had no problem gaining funding. There were a bunch of intro-TA slots open, and the ones who chose not to pursue TA were able to get an RA just by talking around to profs before the semester started. Admittedly, last year's class was a little smaller than this year.
You basically have have a month (around Oct) after class starts to find and secure a 50% appointment as a TA, RA, or PA (project-assistantship)... so moving early to Madison is not a bad idea (though leases here start 15 Aug). A 50% appointment earns you tuition remission, meaning you don't have to pay tuition. You're doing work to better the university, so part of your compensation is a tuition wavier.
Feel free to contact me (see my website link) if you have any questions. I was one of the grad student weekend organizers.
Cheers!