>Furthermore, there is a rash of jobs that are primarily cost-cutting measures from companies based out of more expensive areas, which puts you at a kind of career positioning disadvantage

Does/will the midwest not have this problem though?

>jobs seem to regularly pay under $100k for senior developers here when the cost of living has gone up dramatically compared to my perception that I could get a decent place for <$1500 / month where I wouldn't have to suffer from a horrible commute - this is patently untrue I've found after spending a month searching for housing (not apartments, admittedly).

You can rent a family home on the north perimeter for around $1700 a month. Not nearly as cheap as some midwest locations but not nearly as expensive as the Bay Area. You also do have the option of having a 40 minute commute and paying a fraction of that in rent. It's a nice option to have on the table especially if your job is located outside the city or allows remote days which is often the case.