Please allow me to weigh in on the COBRA and private insurance question. First let me say, I am one of the "early retirees" having left at 52. I never considered hanging onto the insurance through COBRA and I would recommend strongly that no one else contemplating leaving before 55 do so either. The reason I chose to go immediately to private insurance was my concern of how insurable I or my spouse would be at the end of COBRA coverage if either one of us was diagnosed with a malady during the 18 months COBRA was in effect. Remember, there is no guarentee you'll be offered coverage by this insurer after COBRA expires. For example, if you had a heart attack 9 months after leaving UPS and then started looking for private insurance when COBRA got close to running out, how difficult do you think it would be to get coverage in light of your recent heart problems? I can tell you, if not nearly impossible at the very least extremely expensive. And if you had gone with private insurance to begin with? No penalty in future payments, just the normal annual increase based on the claims history of the insured population as well as factoring in your age. As an example, my insurance company paid out nearly $30,000 in claims for me as a result of an illness I had last year. This year my premiums only increased $75 per month. The prior year (before I started submitting the claims) my premium had increased $60 per month. Both the normal increase passed on to all insured's in the group. So I'm confident I wasn't personally "penalized" for the $30,000 paid by the insurance company. You should be financially in good shape if you're considering an early leave. That being said, in my opinion it's not worth the gamble of saving a few bucks for 18 months if in the end because of some medical misfortune during that period, you wind up being close to uninsurable and pay outrageous premiums for the rest of your life. Buy the private insurance now, while you and your spouse are both in good health and avoid the worry of whether you'll be just as healthy 18 months from now.