We've always been able to get our Ent book by the time, if not before, the old one has expired. Maybe start checking the website in September or October--it doesn't take long to ship, so even if you get it in early November you'd be ok.
BTW, we lived in Madison for 2 years (many moons ago) while my DH went to grad school. How we loved married student housing!
And we also loved the Orange Custard Chocolate Chip ice cream from the ice cream place on campus.
T&B