The only thing I can say about getting to Medicare is that you need to understand the difference between the Medicare Advantage Plans, Medigap Plans, "wraparound" plans where you retain your employer's coverage after retirement and Medicare becomes primary, the insurer becomes the administrator.
I cannot repeat often enough "there is no free ride" - an Advantage Plan with a tiny, or no, premium, will definitely not offer as much as a Medigap plan, will have more restrictions, a preferred provider setup, and higher copays.. And usually, if you qualify, a wraparound where you keep your original insurance carrier tends to be best.

Sit down and do some future math. Try to look ahead 15-20 years - what afflicted your parents and older siblings may well come your way. Don't be swayed by shiny perks like "Silver Sneakers" - if they're in your "best fit" plan fine, but if you can't afford your meds, a gym membership is no good to you.
When I became Medicare eligible, it was clear that with a few health issues, we were going to continue to have rising health costs as we age. And an abundance of PT to keep my body moving would be needed.
So low copays were important - in good years we view the higher premium as a "down payment" on future needs. In bad years, we breathe a sigh of relief that we didn't have to dip into savings to cover medical bills.
We also planned to (and do) travel extensively, so we needed portable care - driving 1500 miles to get a lung infection treated is not an ideal situation.
Prescription copays and the most general possible formulary are important too. The meds you need at 80 are often much different than at 65.

Medicare may be the single greatest reason why the life expectancy of our WWII and Boomer generations rose so rapidly. My grandparents and their siblings only had the GP, who listened to their lungs, prescribed penicillin, and got $5 a visit.