A bit longer than me! I started with a home server and then desktop/laptop system with Potato in 2001. I still have the complete Potato CD set.
One thing about #Debian #AFAIC -- and likely most #GNUnix/Linux #distros as well: I found #upgrading between #stable, #testing and #unstable to be #problematic, the more #packages I had #installed BEFORE the #upgrade, and the more I had used the release.
I usually wait until the new stable is ready and then upgrade. If everything seems to be OK, I then dist-upgrade, check again. I've never had any problems. As most of my systems are remote servers I have an anxious minute or two if an upgrade also requires a kernel update (and thus a reboot).
I once had a upgrade go wrong on my laptop, but that was due to me installing some packages from Debian Multimedia that had dependency problems in the testing version I was moving to.
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