I’m personally really happy people are interested enough to both try installing old operating systems using old hardware and blog about it!

There are links at the end of each page and he does literally upgrade the same install up to the last.

It's a great read but...

I run Debian since version 1.1 (not 11 but 1.1) or so (and I was using Slackware before that) and I always re-install my entire system from scratch. I never ever upgrade.

YMMV but to me if you upgrade if either the old (with all your configs) or the new version has a security exploit you are toast. While if you re-install from scratch, you're only toast if the latest version has a security exploit.

Also it helps to keep my skills sharp: I'm forced to re-install and re-configure everything and I like it. I use the opportunity to enhance my shell scripts, to learn new stuff, to do a few things here and there in a better way, etc. FWIW I'm not on Trixie yet (except on one NUC): I need to switch one of these days (and I won't upgrade).

Now the usual disclaimer... I don't claim my way to be the way: to each his own bad taste.

This series of posts highlights one of the features of Debian that's occasionally handy: you can usually upgrade between major stable releases in an automated way.

It can be good for workstation laptops, and for pets-not-cattle servers.

Stability for a couple years, then in-place upgrade to newer versions of things all at once. Whenever the timing is good for you (because you can keep using `oldstable` for a long time, with security updates).

Whether this upgrading incrementally keeps working smoothly for decades, I haven't read all of OP's posts to find out. But I've had machines running well after a few major upgrades, and even moving the HDD/SSD between upgraded laptop hardware.

I also started with 3.1 as my very first linux experience. I never felt the need to change distro over the years. Just yesterday I upgraded 3 servers to debian 13, one from debian 11 and one from 12.

I wish I had more stories to tell, but that’s the thing I like about Debian.

after upgrading dozens of servers I'd say the biggest pain is if someone installs dpkg package manually and not from a repo

also some very old repos went away over time, so your best bet is to always use the official debian repo, maybe with one extra containing software that should be on that server

with that said, it's one of the painless upgrades you can do

Ah, it was amazing compared to Woody. 2.4 kernel as default (with Woody you had to run bf24 at LILO's prompt) and some nice additions such as Gnome 2 and the Linux Gazette magazine as TGZ (among others). I think it had a very polished KDE3 too, it was a breeze to run it.

On games and media, I used to compile a more up-to-date MPlayer from tgz among some restricted codecs and, OFC, Wine/Cedega from CVS.

That was a really cool read (all the way through all the updates).

It's amazing that there are archives online for the old versions, or maybe it's just amazing to someone using FreeBSD which seems to drop old versions very quickly (when 13 was out the 11 repos were nowhere to be found).