Require health insurance assistance

[mikalina]

All good responses. I guess I am the only one who likes to find loopholes.

Another suggestion (especially if you are a poker player earning a high taxable income) is to look into (here come 2 different names for the same thing) a high deductible health plan or a consumer directed/driven health plan.

Downside: high deductible (~1200/year for individual coverage)

Upside: all preventive care visits are covered for free (checkups, lab work, etc), you have access to an HSA

HSA is a Health Savings Account... think 401(k) but you are allowed to make withdrawals without penalty for health-related purchases (anything down to Advil qualifies). This is just a really slick tax shelter with a $2,900 annual max for tax-free contributions.

And the plan should generally be one of the cheapest available.

Edit to add: deductible is not ~1200, its >=1200... the higher you go the cheaper it gets. Sorry for the confusion.