It's more complicated than that. I'd replace "usually" with "sometimes", but you also have the issue of what the overall state looks like. So you can have a "liberal and progressive" city in the middle of a fairly red state, and you end up with a liberal mayor but a conservative governor and legislature, which are constantly stymying your city's attempts to do progressive things. See WI for example.
the biggest Midwestern state by population is Illinois, which is blue, it is where both Lincoln and Obama came from. So, saying "Midwest is conservative", while the biggest state in the Midwest is actually liberal is kinda silly.
not all, but 65% of the voters are blue. I mean, it doesn't get any more blue. Every blue or red state is like that, no state 100% homogeneous. for the purpose of this discussion Illinois is no less blue than any other blue state, so political conservatism has nothing to do with the startup situation.
No, it’s not. Minnesota is blue. Wisconsin is purple. Illinois is a solidly blue state and the biggest in the Midwest. Iowa is purple. Look at this map and tell me again Midwest is politically conservative ? https://en.m.wikipedia.org/wiki/Red_states_and_blue_states#/...
Trump carried WAY more counties in 2016 despite losing the popular vote. That alone should tell you the map isn't a good representation of overall sentiment. Plus, Trump v. Hillary isn't necessarily a good proxy for "conservative v. liberal."