[buff-a]

If you lose your job you may have to pay a lot more (COBRA) for a limited time

No, you'll pay the same as you were paying. Its just that before, you thought you were being paid $100,000 when in fact you were being paid $120,000, and out of that came your health insurance and the other (more-than-) half of your social security and income taxes.

[awolf]

You pay 10% more on COBRA than your employer was paying on your behalf. But the gist of what your saying still stands.

[quatrevingts]

Plus, COBRA payments are (generally) not tax-deductible, so add another 30-40% more.

[buff-a]

A self-employed person can deduct health expenses against gross income. You are correct in that COBRA cannot be deducted in this way. But it can still be taken as an itemized deduction. I'm not a tax accountant, but my tax accountant is. Another gotcha: if you're taking the 60% markdown on COBRA from Obama, then no, you're not allowed to write it off at all, but I wouldn't be complaining about that.

[quatrevingts]

Only the portion which is greater than 7.5% of your gross income can be deducted on Schedule A.

[driverdan]

If you have a HDHP with an HSA you can pay COBRA from the HSA tax free.

[Intermernet]

I'd suggest that just using the ~$100,000 salary range as an example has shown that you're not really understanding of the "average" employee.