I started with Windows 3 and have, not always immediately, eventually moved to the next version... usually when building a new computer
I use a program to make a complete backup, including the hidden files that Adobe uses for registration, so the one time I had a boot drive fail, I just put in a new drive and did a restore, loosing very little data - TeraByte Unlimited :: TeraByte Drive Image Backup and Restore Suite :: Image for Linux has a routine to create a bootable CD
I now use Windows 10, and the only "oddity" I've found is that my wife's computer (also Win10) and my computer sometimes loose our home network connection for awhile when one of us does a restart for some reason... which Win10 has always "fixed" when I restart the other computer so they are back in sync
John I use Shadow Protect, after being put on to it by the lads in the Prem Pro Hardware forum several years ago. It has saved me twice after drive failures. It also has a boot drive image option that can be activated via a bootable CD or USB drive, but sad to say I have never made use of that feature.
As for the crashed system, I am loving that my CC Libraries were all there on reinstalling my CC apps. I thought I used the Libraries fairly extensively, but we apparently get 20Gb of file asset space, and I'd barely made a dent in it. I didn't like that I'd lost my custom workspaces though, and Windows was not quite as clever as I'd expected at remembering my mail account settings. Google Chrome was another success with the fresh install looking exactly as it did before my system crash.
On the whole, I wish I'd gone for the clean install weeks ago, as everything is so much cleaner, faster, and more reliable, and it was nowhere near the hassle I'd expected. I'd have obviously still have preferred to have had complete control of the process, and the chance to save my App Data file structure which is where I think the Adobe app workspaces are stored.