You're assuming that those "benefits" aren't something that can could leverage the scale of an entire country's government. The biggest example of a benefit that's cheaper for a company to provide in bulk is healthcare, and basically every developed country has demonstrated that it's cheaper to let the government handle that. Pensions, paid days off, childcare, and others all make sense to provide at a societal level rather than relying on a company to do right by its employees.

I’m not assuming anything, I’m talking about what you could reasonably expect today of your company if you made this tradeoff.

What you were able to do with that cash is a separate issue. Over time it could become better, sure.

I hear this point a lot about the power of group purchasing. If everyone purchased their own insurance the market would be larger and be able to offer larger discounts.

Doing it at the company level doesn't make sense. Companies with larger sizes have better leverage under this model.

Would the purchasing power be greater at the state level or federal level?

I don’t think it’s purchasing power so much as risk pool. Or really a bit of both, it’s number of healthy vs unhealthy people in the pool. Employees of a company tend to be healthier. People on ACA tend to be part time / low wage, and have more health issues. Insurance companies pass that through by charging based on risk. I imagine what would happen is this would average out, the total cost(including employer contribution) would go up for most of the hn crowd who can afford it, but down for others who currently can’t