Re: Getting closer to time to retire?
Very much the same thoughts I had this time 5 years ago.
Your checklist mirrored 90% of mine.
I looked at W10, Server 2016 and where MS was going with Azure and decided it was time to GTF out which I did the following September.
Never regretted retiring at 63.
I got my Electric Car in 2019. Still brings a smile to my face when I put my foot down. Instant power.