So, I just left the status of "employee" and plan to live off the rental income from my two properties - which will be pretty bare bones meeting my expenses. In the past, as a full time employee with employer sponsored health care, I used Schedule E (supplemental income) for my rentals. Now that my rentals are my only income, and I am more actively doing property upgrades, and I am paying for health insurance out of pocket (ouch) with Obamacare, could I switch over to a schedule C small business schedule and somehow deduct my health care expenses? These premiums are high and it would actually be of great help! Any advice provided is much appreciated!