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Here are some assumptions to help evaluating the choices above: Individual has a HDHP (High Deductible Heath Plan) that is HSA-eligable ($2,500 deductible). Individual has a 401(k) account, a Roth IRA account, and an HSA account, but not enough income to maximize contributions to all three...

I have a question about HSA accounts: Imagine a scenario where I contribute $500 to a new HSA in February 2009 and then pay $1,500 in medical bills in July 2009 with money from a regular checking account. At the end of the year (December 2009) I contribute $2,000 to my HSA. I now have $2,500...