Letters to the Editor
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Midwest is mostly good
The Midwest is indeed a great place. Good people. Good work ethic. People aren't as caught up in trends and status as the coasts. Much of it is beautiful once you get used to not seeing oceans or mountains. (But lots of lakes, rivers, and hills!) Housing and schools are overall good, and the climate is okay if you can stand the winters.
But there are pockets not accustomed to lots of people moving in. For example, I grew up in Green Bay, WI. In many ways, it's a good community. But it's a bit insular and large segments of the social world is in the Catholic church.
There are other parts of Wisconsin where this is less true. Madison is the obvious one, but Appleton and the Fox Cities are decent. Milwaukee is a mixed-bag. It has established suburbs; just don't live in Republican-dominated Waukesha County. The college towns of La Crosse and Eau Claire are nice if you want a smaller feel, but they are more isolated.
For other cities in the Midwest, here are my judgments. All are big enough to have enough transplants to be able to fit in:
Twin Cities, MN - Good schools, housing, coops, lots of culture and restaurants, and even a decent seafood store. Progressive community in a progressive-leaning state. Cold in winter, near-perfect summers. Okay transit. Increasingly diverse. International airport.
Chicago, IL - Obviously big (good and bad), better transit. Culture, nice neighborhoods, a little pricier (but better than Orange County), Lake Michigan, progressive, yet corrupt politics. Diverse. International airports.
Des Moines, IA - Somewhat progressive, respectable size, but more isolated and less diverse. Less cultural/food/entertainment amenities. Slightly milder winters. Not sure how many transplants come to Des Moines.
Iowa City, IA - Has all the great stuff that comes with a college town, but it's still a college town. You'd get tired of the frequently drunk 20 year-olds. At least in Madison and Ann Arbor, there is a bit of a buffer non-student population. Iowa City is also a bit isolated.
Kansas City, MO - Not all that bad. Decent politics locally, but in a scary state politically. (The Kansas state side ain't that much better.) Good size with growing job market and good quality schools and affordable housing. Mild winters, great falls and winters, slightly oppressive summers. Lackluster transit.
St. Louis, MO - A bigger, muggier, not quite as pretty version of Kansas City. (I'm sure I just insulted a large number of Missourians.)
Indianapolis, IN - Like Kansas City, good city in a cruddy state. Cruddy in political and cultural terms. Mild winters, good in other seasons. Some culture (art) and diversity.
Ann Arbor/Lansing, MI - Good progressive communities that are close enough to the benefits of Detroit and an international airport.
Columbus, OH - Another mid-sized college town with progressive politics, good schools, etc. Better housing and job market than the Republican dominated Cincinnati and socially conservative, blue collar, but Democratic Cleveland.
Communities I'd avoid: Quad cities, IL/IA (ugly), or many of the outstate IL cities (Rockford, Springfield, etc), Omaha, NE (boring), Duluth, MN (Too damn cold), Green Bay, WI (conservative), Detroit, MI (it'll get there eventually), Springfield, MO (frighteningly conservative), Cincinnati (Republican).