I'm far more curious about what will happen when these companies start seeing significant portions of their workforce facing expiring option plans...

Is that a thing? I didn't know options can expire, what kind of an expiration date do they have?

It's common for companies to have a 90-day window to exercise your options after leaving the company. There are some friendlier companies with longer exercise windows. See: https://github.com/holman/extended-exercise-windows