We are self-employed. We started our business in '05 and I worked full-time at another job until 12/12. Through that job, we received great health insurance with ZERO premiums and a low deductible. By '12, our business had grown to the point where there was no way to grow further without me quitting my job and joining our business full-time. I had calculated that when I quit, it would cost around $500/mo to insure our family.
I planned quitting for 6 months. I saved $50k in anticipation. I set 12/20/12 as the day to hand in my notice. I found out on 12/13/12 that I was unexpectedly expecting my 3rd child. Since this was before ACA, I was immediately disqualified from getting insurance on my own, as were my husband and children. After a few weeks of major stress, I finally cobbled together a plan in which I got pregnancy Medicaid to cover me and my unborn baby, paid $1500/mo for COBRA to cover my husband and me (this was the only way to get my husband covered), and got my existing kid on Peachcare (a GA program that is for people with an income higher than the Medicaid limits).
I won't lie - it really sucked. It ate up $1k extra/mo that I hadn't planned on, on top of the pregnancy related expenses. There were two reasons why we were able to make it work - (1) our business was established and growing so we knew we could reasonably expect to make a certain amount of money and (2) we had saved a significant amount of money to cover several years of income shortfall.
In your situation, AFAIK you will not qualify for ACA because your wife has the opportunity to purchase insurance through her work. So, the rest is moot. The question of self-employment is essentially a mathematical equation: your projected income + your wife's income - health insurance costs - living expenses = monthly surplus/shortfall. Project how long it will take you to turn the shortfall into a surplus. Multiply your shortfall by that amount of time. Save that amount. Then quit your job.
By the time you've saved up enough $, you'll have a pretty good idea of what is going on with the healthcare situation and can adjust your plan accordingly.