I've been self-employed since 1990. The lack of affordable health care has been by far the biggest problem (I'm on Medicare now). Alone among modern economies, the US insists on tying health care to insurance, and of affordable health insurance to working for a corporation or government. I don't want health insurance. I don't want health insurance to even be a thing. Other countries do just fine without it, and they have the health outcomes and life expectancies to prove it. Our tax laws are byzantine. That's another feature, not a bug. I'd go a little further and propose a universal basic income. That would take care of most of the rest of your list.

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