When I can make insurance elections again, I'll be having this consulted for then done in the beginning of the year. Likely Spivack.

A coworker recently told me that when you elect an amount of money for Flex Medical, that amount is deposited into the account on Jan 1 of the new year, and the per-paycheck amount is removed throughout the rest of the year. So I'll be paying for it pre-tax and whatever discount VSP gets me.