Actually I found Chicago to be extremely affordable, and really lively. The absolute friendliest people on earth.

If remote work holds up I expect to see San Fran's real estate market, at least it's rental market collapse

One of these reasons is often the lack of jobs. Suburbs are actually often fairly expensive since they try to bring the good of the country (individual houses, bigger lots) closer to the city where good jobs are located.

Public transportation.

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.