[rstuart4133]

I use Debian stable. I'm utterly unafraid Debian's security patches, in fact I just accept them on my home server boxes without inspection. The same can not be said for Windows - I'm seen Windows security upgrades render boxes unbootable.

Moving between between versions is a different matter. Yes, Windows does it better, but not reliably enough for me to trust it. So for both Debian and Windows it's a case of replace the drive, and do a fresh install. In Debian's case, zstd < /dev/sda >/mnt/usb/sda-backup.zstd also works, if you have time to kill. Copying everything to a squashfs image also works well.

If your using Ubunt then your experience will be different. People who choosing Ubuntu over Debian is as perplexing to me as people voluntarily using Windows.