[jcranmer]

If you get health insurance via your employer, the value of that health insurance is not considered income, and is tax-free. If you pay for it yourself, you get no tax benefits for doing so.

That kind of skews incentives a fair amount.

[gregkerzhner]

This is not true (at least if you are a contractor or are self employed). You deduct your health insurance premiums (and all sorts of other expenses like home office) as business expenses. After that’s done you pay tax on the rest. source - I’ve been contracting for 6 years and buying my own insurance.