I'm changing jobs the end of June. I'm 58 1/2 years old. My current employer, a relatively small non-profit, pays all of my premium for a catastrophic medical insurance policy with a $10,000 deductible and an employer HSA that reimburses the first $700 and the last $6000 of the deductible. Since I will no longer be an employee, the COBRA insurance will not have that benefit, so it will really be a $10,000 deductible, should I need medical care. (for my teenage son, I opted for a private BCBS policy with a $5000 hospital deductible, but covers outpatient doctor visits less a $20/$40 co-pay.) I will not be eligible for medical coverage through the new job until I finish the 3 month probationary period. I know from experience (had another company fold under me 2 1/2 years ago,) that it will be 3-6 weeks before I get the paper work about Cobra insurance and what that might cost. If I elect to pay for Cobra coverage, it will be retroactive to my last day of work.

I will also be without a pay check for approximately 5 weeks and will have to use my credit cards (shudder) to compensate during that period, with a plan to pay them off quickly during my first 3 months of employment, when I will have no benefits, but will also not be paying for any of those benefits.

Given the $10,000 deductible and the likelihood the Cobra premium will be several hundred to close to $1000 per month, I have been thinking that I would probably opt out, and go 3 months without medical insurance for myself. I have some medical issues that I have been putting off dealing with due to the deductible, but nothing that I don't think can wait for another 3 months. (The new job has much better insurance.)   

Then, this weekend, for the first time ever, I missed being the 4th car in a serious 3 car accident by about 6 inches, a split second, and pure luck. I did nothing to cause the accident, and could do nothing to prevent what I had resigned myself to be a head-on collision at 65 mph. A billiard effect occurred among the three cars that did hit and wreck, clearing my lane at the last possible nano-second. Needless to say, it has got me pondering going without medical insurance for 3 months, even with a high premium and a $10,000 deductible.

Who has been confronted with a similar situation regarding medical insurance? What goes into your assessment of risk tolerance vs risk aversion?