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where my health insurance premiums are pre-tax ($3500) and I have a flexible spending account($5000), which is deducted off my income like a 401K. For the 7.5% threshold, can I include the $8500 as medical expenses, plus my un-reimbursed medical?

Nope. Those have already been deducted from your income - they were excluded from your W-2. You can't deduct them again.

--Peter
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