> But if we passed laws to change these expectations (Obamacare is at least a step in this direction) so that companies just paid cash and it was reasonable to set up these things yourself, it would make workers' lives so much simpler

You can go one step ahead and make it completely automatic: you get health insurance the moment you are born. You retire the moment you need to. You are automatically insured against unemployment and other mishaps. You get free schooling for as long as you need. It can all be funded by taxes, personal and corporate.

It works in Europe. It should work for the US.