STP: Please come in__Tax quesitons about 1040-X for experts

I am a research associate at University, when I choose the health insurance tax staff back in 2004. I choose th default option -after tax, because I don't know it is tax exempt,it only has two options, pre-tax or after-tax. but this year I knew what is going wrong,it is tax exempt in deed. I thought the university options for this item is misleading to me no tax exempt option at all. so I am planning to fill the 1040X to IRS and ask back this money, it is more than $1000 dollards in total and it is a big money for me,


(1)Do you think I can win it? any suggestions will be appreciated.

(2)Do I need to ask our HR to redo my w-2 for the last three year, if they reject me, then what will I use to show IRS for this money refunding? Any regulations or laws I can use to fight for this?

Thanks.