You can't escape Healthcare and Taxes

[Anthony R.]

So I'm in the final stages of living 100% off of my rentals. As I prepare to take the final steps (probably in the next 12 months or less) I'm trying to answer a couple nagging questions I have.  

First, is there any tax surprises when leaving a W2 job for rental income? Currently my rental income makes up about 75% of my annual take home and it has been increasing to that point from 0% over the last 5 years. I have a CPA do my taxes each year so assuming he's not screwing me, I anticipate that it shouldn't change that much. However, I don't know and I'm curious what others have experienced. 

My second question is, what does everyone do for health insurance? I went from my parents health insurance plan, to the Army, to whatever plans my W2 jobs provided. I've never had to buy it in the private market so I'm not sure what to expect there.
(Just for me, no dependents, 31, extremely athletic, so I'll probably want something that can handle hospital visits)