There are really two "Midwests"-- and more if you count the plains/mountain states (I don't) as part of the Midwest. The rust-belt (Detroit, Milwaukee) is in bad shape, but Chicago, Minneapolis, Toronto are solid places. So are Madison and Ann Arbor-- top-5% mid-sized cities.

The Bay Area I would fold into the Pacific Northwest, since it's culturally a part of that region, although it has a lot of California's problems (expensive housing, budget crisis). It's more similar to Seattle than to L.A., I would say.