I have a client in a similar situation - sort of. His employer has 6 employees, so he was required to go on Medicare when he turned 65. Medicare is primary, and the employer plan (which he gets free) is secondary. He has an MA only plan, and the employer plan gets the bill for copays and provides creditable drug coverage (similar to someone who has Tricare for Life and an MA only plan). When he retires he can use LEC to enroll in a PDP. UHC tells me that he will also have GI for a med supp based on losing employer coverage, as long as he applies within 63 days.
I did read that he has a 63 day GI period from the date of loss of coverage no matter when he took out part A and B . I was always under the assumption you had a 6 month Iep window for med sup from the time you signed up for part B . I didn’t know if you have part A and B and group coverage and you retire you have a 63 day Gi period . But as another poster said you won’t get paid doing that in most states if he needs the Gi.