Regarding the self-employed health insurance deduction, section 162(l)(1) of the tax code says: "there shall be allowed as a deduction under this section an amount equal to the amount paid during the taxable year for insurance ..." There doesn't seem to be any mention of a requirement that the payment to be for insurance coverage for that same year. You'll still need to have sufficient net earnings from self employment on your tax return to cover the entire self-employed retirement deduction on that same tax return.
