health insurance - hsa - unemployed - self employed

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BEST tax savings on health insurance?

My wife has her own schedule C small business web designer business. I was receiving unemployment for the first four months of 2010. We have a new HSA we are setting up. Before April 18th 2011 I want to contribute an amount to the HSA equal to the valid costs I incurred in 2010 to get reimbursed from the account. I believe I can get reimbursed through the HSA for the insurance premiums while I was receiving unemployment.

My plan at this point is to run the premiums for Jan - April (period receiving unemployment) through the HSA.

Deduct the premiums for May-Dec on 1040 line 29.

Can I deduct Jan-Apr on line 29 as well, if I am going to get reimbursed from my HSA?

If I can only do one or the other, are the tax consequences the same whether I run the Jan-April through the HSA or include on line 29?

We have a fair amount of revenue in schedule C with unfortunately very little expense so there will be no issue with making enough income from our schedule C business to be able to report the HSA contributions and the insurance premiums.
 
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