I agree with your overall point that the U.S. medical system suffers from overregulation. We could (and should) allow more primary care to be performed by, for instance, qualified nurses, RNs, and nurse-practitioners. As you point out, the existing guilds hate this idea.

But your first point needs some correction. Health insurance is only tax-deductible when it's paid for by your employer. [EDIT: Just noticed you mention this lower down, but your first paragraph gives a misleading impression.]

This is perverse in multiple ways. There's the way you mention: that it subsidizes health care over other forms of compensation, so we wind up spending more on health care than we would otherwise.

But also, with particular relevance to HN, it subsidizes employment over other kinds of work. If you leave your job to start a startup, you lose a substantial tax advantage.