Portland

Why is it always blue?

Because overseas real estate investors don't want to lose money, so they invest in places of value. They're certainly not investing in bumblefuck Alabama.

Capitalism sucks the life out of nice things.

Agreed. In many of the bluest places there seems to be a lot of NIMBY-ism. So, while it used to be an affordable place to live, the older folks that bought their homes decades ago don’t want their home prices to go down. This seems to make things like re-zoning for multi-family (or denser) housing, restricting car parking, etc. much harder than it should be.

It feels short-sighted because living in a dense, walkable city is a really great experience, and it’s the only thing I miss about the East Coast. Everything else there I’m glad to be away from.

I’ll admit to not having seen the lion’s share of Portland’s neighborhoods, but the most walkable ones seem to be closer to the river. However, there’s no reason this can’t spread from there if we actually allow it too. Neighborhood bars, walking distance to a grocery store, more parks, MORE SIDEWALKS, etc.

Also, Minnesota is amazing.

Minnesota ... is affordable

Is it? Rent costs in Portland and Minneapolis look almost identical.

In either case it's because cities are hot real estate markets and capitalism erodes social policies that stand in the way of market access. Doesn't have much to do with red vs blue.