Anyone in a high tax bracket will likely come out ahead on an HSA/HDHP (high-deductible plan). We’ve had some “big” years in terms of medical expenses and I’m confident we’re still ahead with the fully funded HSA account.

The key is you don’t pay for healthcare expenses with the HSA, but instead pay with after-tax funds and save the receipts. Later (many years later), you can take out the HSA money and spend it in retirement tax-free (up to the cumulative amount of medical receipts you’ve paid and accumulated).

Used this way, it’s a retirement account (one with hands-down the best tax treatment), not a health care savings/spending account. To get it you have to have a HDHP and cover the expenses along the way.