My health premiums from a public employee job have gone through the roof. 2016 is the last year for Chicago to pay a subsidized portion of a retirees healthcare. Premiums for myself and wife is 1600 a month. This is outrageous. I am wondering if it is just better for me to self insure. Knowing this is dangerous because one of us could get cancer or some life threatening disease which could bankrupt us. I was thinking instead to bank up to or close to the 1600 monthly and just pay the penalty. Isn't it true that Obamacare has to take anybody regardless of their current condition? I understand that their would be a 90 day delay though and in the meantime would have to pick up those current expenses. My pension and her social security is plenty for us to live on and I have a mid six figure amount in taxable and 457 accounts. Is this rolling the dice or am I on to something here. We are 4 and 5 years away from medicare and would be saving almost 20,000 in a year where we would use limited medical. Any thoughts?