Would I be eligible for any type of special enrollment circumstances if I have health insurance with my employer but quit my job voluntarily and/or retire?
If you quit your job or retire, you'll get a Special Enrollment Period allowing you no less than 60 days to enroll in the Marketplace before your employer plan ends.
Please note that if you lose your coverage, for any other reason other than non-payment, fraud, or misrepresentation, you are typically granted a 120 day special enrollment period. This period typically starts 60 days before you lose coverage and lasts 60 days after.
This said, employers only need to offer 30 days for special enrollment in employer coverage (getting a plan from an employer, not losing a job and getting marketplace coverage). So if you have a baby, or a family member loses a coverage option, the employer must offer 30 days of special enrollment for all qualifying life events.
Each special enrollment period is technically different (even though marketplace enrollment options generally share the same timeframe), so while the window is typically 60 days, you'll want to double check depending upon your situation.