But support for W10 is going to stop, so we will all have to totally upgrade our systems, and we know how many problems that will cause, because however much beta testing they do it still cannot replicate the billions of different uses that the system is required for.
Windows is still annoying for various reasons, but it handles updates and upgrades with aplomb.
My sons computer started as Windows 8.1, was moved from an HDD to an SSD, then to a new motherboard (completely new chipset and CPU including a change from AMD to Intel architecture), and is on it's 3rd gfx card.
At some point it had an "in place upgrade" to Windows 10 (not a reinstall), and many monthly patches and bi-annual OS updates. All without missing a beat, and it gets a lot of use. A hell of a lot of use.
You're absolutely right that a new OS is a significant change, not guaranteed to be painless, but the upgrade process and "plug and play" capability is light-years ahead of what it once was.