As someone from a "cheaper country", a crazy amount of these jobs dries out when they figure that they'll need to deal with your tax/labor law employment situation.
There's still plenty of remote work, just make sure you don't go into this completely blind.
https://en.wikipedia.org/wiki/Professional_employer_organiza...
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.
Why not make your laws more friendly?
Frequently the issue isn't so much that compliance is extraordinary difficult, it is that there is no section in the HR manual for handling it, and they don't want to deal with it. Most of the time it would take two days of labor at most, and a small percentage of the employee salary to make it kosher. In Canada it is so common that there is an entire industry that will arrange legal employment of Canadians by foreign corporations with no local presence. Most US companies don't even want to hear about how easy it is to comply.
I guess the existing rent-seekers wouldn't like it however.