Funny, I have now transitioned to Windows 10 four times. One time on my personal computer. Three times at work, as part of a corporate upgrade. I am impressed with the quality of the upgrade experience Microsoft has built into the OS. When I first moved from PPC phone to the iPhone, I was shocked at how easy the upgrades were. It bothered me for a time how much easier the consumer-focused upgrades were. I realize that they were a consumer (iPhone) versus in most cases enterprise (computer OS) so the migrations are handled much differently. Until Windows 10, in fact, I would say that was always true.
I’ve now upgraded some PC’s in the past two years, and frankly, Windows 10 is a good upgrade experience. I will say that the two PC’s I have that were built for Windows 10, the Surface Book and my basement VR computer, perform extremely well. They are optimized for the experience. I like the surface book pen. It is comfortable to hold, and like the Apple Pencil, it is really easy to use. I am not an artist, but I use the pen to write on PDF files people send me.
All of this as a roundabout way for me to say I was wrong about Microsoft and their ability to produce a decent upgrade experience. What I need now is the same process for a couple of other devices. That isn’t going to happen, and I won’t shame the products. Upgrades are so different now compared to how they were. The more consumers engage with the product, the more expensive a tricky migration is. The more time your helpdesk spends fixing simple problems, the more expensive it is for your organization overall. Now if the other devices were as easy to upgrade I would be able to sleep nights!