I lived there for several years, OP. I'd like to offer what I think is a fair assessment.
The pros: - It is a lovely city. There's a lot going for it. For a city of its size, it has a magnificent cultural palette and an amazing food scene. State Street and the Square alone are host to a number of cuisines, and there are other pockets through the area that are equally as good. In one block you can find Greek, Asian and Himalayan! - It does have some level of diversity IF you are part of the university community. - There is a relatively active gay/lesbian community there, and a pretty cohesive one. Madison in particular is a LEZ paradise. There's data out there that the highest per capita lesbian population, per zip code, is in the Williamson Street (locally known as Willy Street) area of Madison. - The LGBTQ+ magazine "Our Lives" is one of the best I've read anywhere, quite something for a town of its size. - You'd be hard pressed to find an area with such a wide array of beautiful outdoor spaces, the lakes and Arboretum among them. - Great cultural amenities - the newly renovated main library, the Overture Center, etc. - The Dane County Farmers Market - always a joy. - It remains remarkably affordable and it's possible to buy a condo or house still (though prices are higher than they used to be). - I lived near the university and for the first few years - when I was still enjoying my youth, shall we say - hooking up with hot beefy farmboys was like shooting fish in a barrel. It was GLORIOUS.
The cons: - Outside of the university, there is a sense of provincialism. People are "Midwestern nice" but if you didn't go to Such and Such High School with Mitch Hoopenschoocher in 1978 then it can be really hard to have more than a passing acquaintance with people and make new friends. - Because of that, it can be a terrible place to be a single gay man, if you're seeking a relationship/husband, etc. because a new person is seen very much as an outsider. (And also.....some of the local guys are very much mama's boys, or lived with Mother until they inherited her house at 50, etc.) - Despite looking like a very diverse place on paper, lots of locals are pretty racist and also very sexist...it shocked me how many middle aged men sit on State Street to watch young women walk by. (They're usually nice to gays. Usually.) - As with many cities, go 20 miles outside city limits and you're in Let's Go Brandon territory. (Kenosha isn't that far away....nor is Waukesha, another racist paradise.) - While things are better than in R1's days there still is somewhat of a cap for salaries, and a limited scope of jobs, again, unless you are involved with the university. It's much easier for companies in Milwaukee, Minneapolis or Chicago to attract talent with higher wages and benefits. - The winters. You can't fully appreciate how fucking COLD it can be. I will say it was never 4-5 months of arctic weather in any of the years I was there, but February is just snow and relentless wind and even though it's only 28 days in a month it feels like it lasts fucking FOREVER. - What R14 said. While things are looking up with the governor's office and the new state supreme court makeup, it has been a terrible mess at the state level for 20 years. Lots of MAGA types. It was a state that shot down gay marriage and banned it in the constitution (the main reason I left). The nefarious Wisconsin Manufacturers & Commerce (WMC) is involved with lots of dark money.
I would consider returning or renting for the summer now that I'm partnered. ("I said I's married now!") It is really nice, on so many levels. Not sure a full time return would be right for me but I can see why so many love it.
PS: Students keep things fresh and vibrant but unless you're into being in a 24/7 party scene, avoid living downtown, near campus or in the very near East side area, where student housing is concentrated.
