I've lived in Wi most of my life though I've also live in 4 other states for short durations.
Weather has to be one of the worst things about Wi. I still can't believe how it can be so brutally bitter in the winter & yet have bouts of suffocating humid & hot weather in the summer. You get both extremes & it sucks. You will never get used to winter either. Winter is ugly too because it snows & usually doesn't melt for months.
The roads are all heavily salted which ruins your car & everything turns into this ugly gray dirty snow world where people drink 10 hours of the day because alcohol is practically free in Wi.
https://www.youtube.com/watch?v=7WlwumGkSec
Summer comes quick & it sucks just as much as winter. The worst part of summer is the humidity & heat that lingers at night, which doesn't allow the temp to drop. Last night, it was still 70 degrees at midnight & that makes sleeping miserable.
If you have to live in Wisconsin, then select Milwaukee or a Milw suburb. Weather is better in Milw due to lake effect. Close to Chicago & the city has good housing prices (but high property tax). Milw also has lots of nice parks & lots to do.
I've tried living in Madison twice. Nice town if you're a college student, but other than that you will get very bored. Don't try living in Madison without a car either.
Landscape. Many think of Wi as being a beautiful state, which it is in parts, but there is a lot of ugly flat treeless areas too that are miserable to drive through. Entire stretch from Milw to Madison. Nice parts? Northwoods, along Lake Michigan, sandy terrain in parts of central Wi, Bluffs in SW.