Each business has to stand on its own with regard to having sufficient income to fund and receive a deduction on Form 1040 line 29 for the self-employed health insurance payments. Each business has to have sufficient net profit on Schedule C line 31 to cover the sum of self-employment health insurance deduction, the self-employed retirement deduction and the the deductible portion of self-employment taxes. The business that shows a loss is not eligible for any of these deductions.
