//One of the problems with US health insurance is that it is tax deductible only when "paid" by the employer.//

Healthcare expenses are deductible, but only those that exceed 7.5% of your AGI. So if you are a software developer making $100K a year at a start up with crappy health insurance, you can start deducting expenses once they exceed about $7500, depending on your tax situation. Of course, health premiums deducted pre-tax from your paycheck are not deductible at all.