Earlier quoted context omitted.
> Any reputable tech company (or startup) will provide health insurance ... which generates another dependency on the employer (beyond the work visa thing). I know the history of the employer-pays-for-health-care model in the US, but really: it's broken, fix it.
You already have that dependency in terms of your visa. If you don't work for your employer anymore, you don't have a visa any more, and you need to leave the country fairly quickly or get a new visa elsewhere. In the light of that the healthcare part doesn't matter as much.
It's still broken (like so many other things in the US) and therefore one more deterrent to even considering going the work visa -> green card -> citizenship route.