Wow -- this is a tough question. A lot depends on your health and your wallet! The employer plan will bridge you to Medicare, but expensively. However, if you take the COBRA you will be shopping for a temporary short-term plan in 18 months. If something happens to your health in between you might not qualify for a short-term policy. Much as I hate to advise you to spend the money, I'd probably go with the employer's plan. Or else, look for a part-time job that offers group health insurance through a small business.