If you're in insurance, you should really consider Columbus. Minneapolis is wonderful. Madison is wonderful. Ann Arbor is lovely (and I say that even as a Spartan). Grand Rapids has a very nice reputation. I was born in Fort Wayne; I moved away when I was 4, so I don't personally know much about it, but even by Midwestern standards it has a reputation for being dull.
IMO, though, you can't go wrong, and I'm jealous you have that kind of flexibility!
Columbus is definitely on my list. It has a better economy than Ohio's other big cities, is attracting young people, has a large insurance job market, and is a relatively safe city. Have you been to Columbus before?
Yes, I lived there for two months last summer. It was excellent! Very easy to get around, plenty of nice restaurants and bars. (And dive bars, which are more important than nice bars.)
As someone who's lived in the DC area for almost 5 years, well, lol
but, yes, those cities are
more expensive than the ones on your list I suppose. You should actually find a cost of living comparison calculator online to check your intuitions.
EDIT: Oh! I saw that you indicated that you're interested in taking public transit. Columbus doesn't have great public transit, but they are rolling out a redesign of their bus system that's similar to one in Houston that increased ridership there. However, you should know that public transit is just... not a thing in the Midwest anywhere but Chicago (and to a lesser extent, the Twin Cities).
