If remote work holds up I expect to see San Fran's real estate market, at least it's rental market collapse
1. Population decline. 2. A very large amount of good housing stock. Chicago's completely flat with solid public transit reaching out to the suburbs. 3. Lower proportion of tech and startups. Similar to how tech has driven up the CoL in many cities, the relative lack of tech in Chicago has kept CoL down.
Winter is rough in Chicago, but the CoL in Boston has skyrocketed which invalidates that as being the _only_ reason.
Your dollars go further in Tennessee, Florida, or Texas (all of which have no state income tax).
San Francisco's climate, walkable hoods, having a ton of things to do will probably make it come back from the dead even if the tech industry were to actually leave.
Events and opportunities to socialize.
Even if I have a family one day, I still would want my kids to take language classes , etc.
I hate driving ( particularly when commuting), so a town wouldn't really work.