America's Elder Crisis, Medicare Edition

A fresh question for anyone who’s dealt with starting Medicare recently.

My whole life my wife and I have had medical insurance provided by her or my employer. As a result, we’ve always had the same insurance. Good or bad, it was the same for both of us.

She turned 65 couple months ago. I retire on my 65th birthday a couple months from now. When that happens we will both lose our current insurance which comes from my employer.

We intend to do some form of Medigap / Medicare Supplement insurance and are working through the selection process now.

That’s the facts; here’s the questions:

  1. Is there any requirement that we have the same insurance carrier and plan?
  2. If not, what are the pros or cons of doing so?
  3. Does that mean we’ll be starting a whole fresh set of deductibles for just the last ~3 months of 2023, then re-start another fresh set of deductibles in Jan for 2024. In addition to the employer plan’s 2023 deductibles we’ve already met? Sounds expensive.