My wife and I have a peculiar tax situation. She has steady freelance contract work with about $100K per year in income as a sole proprietor. As such, she pays self employment taxes on almost all of that income. I am part of an LLC where 100% of the income is passed through capital gains. This amount is variable but has been about $75K. The result is that I have no earned income and pay no self employment tax. The LLC that I am a member of is offering us the option to buy health insurance as part of a group plan but we would be paying 100% of the premium ourselves at about $1200 per month for a family plan. In the past, my wife has purchased a private insurance plan for the family and therefore taken the self employment health insurance premium deduction for her business. If we buy health insurance through a group plan that was created by the LLC I am a member of, would we still be able to take that deduction? Tax law states that "You can?t take the premium deduction if you were eligible for a group insurance from your or your spouse?s employer." We are in a strange situation because while I have access to a group plan it is not from an "employer" as I am not employed and 100% of the premiums are are paid by the individuals who choose to be a part of the plan.