For me it was:
Windows (for many years) -> Ubuntu (for a year) -> Arch Linux (for half a year) -> Void Linux (literally 2 days) -> Artix Linux with runit (a month) -> Gentoo Linux (another month) -> Debian (finally, I don’t plan on changing it).
Also, when trying to switch from Gentoo to Debian, I fucked up all my data with no backup.
What was your journey?
EDIT: Added Windows
Does a debian version upgrade require an OS reinstall?
For me, no…
I’ve gone from debian 9 to debian 11 and now debian sid without reinstalling OS on my desktop
Same with my servers. Debian 8 -> 11 all upgrades in-place. Will have to upgrade to 12 soon…
The only time i messed up an upgrade is when accidentally used the codename “bookworm” in the sources file and skipped a major version. The system tried to fully upgrade 2 versions ahead and promptly borked itself… But it was an LXC container so i just rolled back my mistake. Lesson learned…
But yeah. Full re-installs have NEVER been a thing for me since going debian. It will even happily clone to a new SSD when you need to upgrade your hardware. (As long as your new hardware has in-kernel drivers, or at least some basic functionality to boot and fix the problem, if any)