For work, I have the occasional need to use Windows. I started out with a Windows XP virtual machine, and when that went end-of-life, I upgraded it to Windows 7. The “upgrade” process was really more of a reinstall-but-with-your-old data preserved. I had to reinstall many of the applications (including Python, though I didn’t realize it at the time).
I don’t pay much attention to the Windows ecosystem, but I had heard that a lot of unseen improvements took place in 7 and beyond which should make the upgrade process easier, so when it was time to upgrade because Windows 7 was (past, oops!) end-of-life, I wasn’t too worried.
Windows has a nice nag every time you log in saying “upgrade to Windows 10!” so I did. But it didn’t like the VirtualBox video driver. I tried reinstalling the Guest Additions, but that didn’t work. I tried uninstalling the driver, but Windows helpfully reinstalled it after a reboot. A forum post suggested I should enable 3D acceleration. Still no luck.
What eventually worked was to update to VirtualBox 5.0.12 (I had been on .10) and then install the latest Guest Additions. Instead of using the “upgrade me!” pestering, I had to download the Windows 10 media creation tool and use that to perform the upgrade.
Once I got those steps figured out, the upgrade process was pretty painless (if a little slow). Everything seemed to work fairly well, though I haven’t given it an in-depth trial yet. I do like the return to a more traditional UI, the tiles of Windows 8 work great on a phone, but I don’t like them on a desktop (and even worse on a server).