I assume you are asking about the self-employed health insurance deduction. You can take that for the months neither one of you was eligible to be covered on the company health insurance. That would appear to be August to December in your case. You can deduct all of the insurance premiums as itemized deductions, accept for any that you take the self-employed health insurance deduction for. Your health insurance is only deductible as an itemized deduction to the extent it exceeds 7.5% of your adjusted gross income. You may not benefit from itemizing your deductions if your standard deduction is more that your itemized deductions.
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