OP here, I've been living in Madison now for the greater part of a month. It's okay, there are many nice things but I'll always pine for my cozy apartment in Kane Co, IL.
Things I have discovered/learned about Madison:
>Navigating the convoluted one-way streets and intersections is still a nightmare, as long as I stick to the same route I'm fine, but if I go anywhere new, I always end up somehow getting stuck on a highway entry ramp
>Apartment hunting really does suck, even amongst my new co-workers, a lot of them are looking to relocate and having a hard time
>The spring foliage really does help it seem less depressing
>Milios is nowhere near as good as Jimmy Johns or Jersey Mikes
>Lunch options in the Shenk/Atwood and Willy Street area are all overpriced
>It's also full of hipsters/hippies
>This town has tons of Asian restaurants, I kinda miss the Mexican fare of the Shitcongo region
>Free public parking doesn't exist, gonna have to take the bus from now on