I have an expensive medical condition, which guarantees I hit the out of pocket max on my insurance every year. With health insurance exchanges, it's now very easy to do analysis on the plans each year to pick the right combination of premiums, copayments and out of pocket maximums. I usually put together a simple spreadsheet with the variables in it, plug in the numbers, and pick the plan which is the lowest total cost.
The good news is that with the ACA, you never need to fear living without insurance. If you're aggressive about keeping your income down, you will qualify for subsidies or possibly free through Medicaid. If your lifestyle is more extravagant, then you'll still be able to afford a plan right up until Medicare kicks in, for a few hundred dollars a month.
Blonde - you should shop the Exchange, too. When i went self employed in 2013, I got a much better plan for less out of pocket than I had with my employer, even including their subsidy. With tough conditions, the high copays, coinsurance and OOP max eat you up.