If you have 2 separate businesses and so have 2 Sch C’s, you can only assign your medical insurance payments to one business. You can’t split the cost. If you have 2 policies, for example one for medical and the other for dental insurance, you could assign one policy to each. If you can’t apply all of your premium payments to your business because they exceed your business income, the rest can be a medical deduction if you itemize.
