I have wondered what would happen if a person got sick, showed up at the hospital and didn't have I.D. on them? Or didn't have insurance? Those are the people they seem to take.
The new health system was supposed to be affordable for those who can't afford it, and herein might be an angle........If you show a low enough income you would qualify for reduced healthcare. You could maybe shelter some of your income in tax deferred investments. A reasonably healthy person could opt not to use any healthcare for a short time and hope for the best.
There are plenty of those quick stop medical treatment places that work on a pay as you go approach. The last few times I went to the doc he looked at me and said...yep, you're sick. Well thanks, here's my copay.
 
I'm no accountant but I know that if you file as an LLC or corporation you have some protections over  a sole proprietor. Could the rental property be assigned as a separate business? This might have advantages.
FWIW turbo tax lets you go through different scenarios before you actually file. It can run multiple versions of your info in different ways to see what works best.