Asking in general to the topic and not anyone mentioned in your post: What is one's occupation? How important financially and to their identity is their job? If they are in good health when they retire what do they want to do? Oh yeah, almost forgot, when they retire how comfortable and secure will their available income be, both needed and disposable.
The most positive thing about the various ones regarding my current and most recent but permanent retirement is not having to ever work again. Not one more F***ing day! Geez, I can't even put a price tag on normally never having to get up or go to bed except when I want to do so.
I have two kids in college and a senior in high school, so, although I'm at a reasonable age to do so, retirement is still a bit away.
A lot depends on what you do with retirement. Like Arc, I look forward to not having to get out of bed to an alarm clock. But staying physically fit and finding some sort of community involvement, e.g., volunteering, seem to help. And I'm of the opinion that those of us who are active on the internet, be it social forums, gaming, etc. will see less of a decline intellectually and cognitively.
Personally I spend two much time on the computer. But after I had retired about 6 months I knew I had to have more structure. So I volunteered to drive cancer patients to their treatments. Needed rides are posted on the internet and you choose which to take. Can stop at any time. But I have always believed in doing what you committed to. So dressing and shaving to take somebody to the hospital is something to look forward to. I often read while they receive their treatments which is something I might have been doing anyway.
I have discovered as I age I like driving in the heavy traffic of big cities a lot less so I am traveling less than I expected. My health is not as much of a problem, YET, for someone who had had two heart attacks and prostate cancer. I see the doctors when they say and mostly follow their directions. When serving as a 1LT in Vietnam I never expected to live out the year so I have had 50 years of unexpected life.
I love my kids and still look forward to every visit. In my case I needed to put some structure back in my life but I still have control of what and when.
My parents passed twenty-two years after my Dad retired. My Mom was always the stay-at-home mom, so the only change for her was my Dad was underfoot more often.
My Dad kept active in the Masons, I suppose that was his structure. They were both homebodies. Never traveled except to take my sister and I places.
Me, I'll be working up until Noon on the day they plant me. Having gone totally broke twice and spending the decade of my life when I should have been my most productive and prosperous on disability and screaming in the closet, there will be no "retirement" for me.