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For the presented situation, the first thing I would look into is a combination of three things:
Would he be willing to wait until Jan 4 to retire?
Would the company allow him to wait until Jan 4 to retire?
If he waited to retire until Jan 4, would the company allow him to have active employment health coverage for the entire month of January?
Ok, I'll admit, I'm lost on the Jan 4 significance.
Any other things I should consider when talking to him? Will having Medicare Part A (w/o B) + COBRA affect him at all - negatively
I don't believe that Cobra insurance counts as insurance from active employment for Part B eligibilty. I think if you go 18 months on Cobra, you are guaranteed to have a Part B LEP.
You have 8 months from the loss of employment/beginning of cobra to grab part B without a penalty.
You are dangerous to the public LD!