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Looking for inspiration/advice/best practices on system upgrade



Hi list,

while still on debian buster (old-old-stable soon), i am approaching the
point, where i will be ready to upgrade. I do have backup(s) from
different points in time, and can carry out restore to a VM, that is
almost identical to my main system, that i can use as a playground for
playing through the whole process.
Also i can automatically set up a running duplicate of my system on bare
metal in another partition, in order to allow investigation of the
process without risking my current working environment.

But i could not yet decide upon the right way to progress, 3
alternatives coming to mind:
1. Upgrade from current configuration using upgrade path tools (apt) and
plan only one step (going to bullseye) at a time, eventually having to
upgrade a second time later.
2. Install a fresh bullseye and try to manually make it as similar as
can be to my current workhorse
3. Skip bullseye altogether and jump to bookworm right away.

>From my past experiences, i recall one problem, that i am still
suffering from: the file group and user owners, that reside on a
different disk set (on a ZFS pool, to be more precise). In order to
alleviate the problem, i did at one point fetch an older /etc/group and
passwd file from a backup and created a mess. I'd love to straigthen
this out now.
At the time, i did investigate (configuration management) tools, but
found the effort was much too high for my liking, as i am the only real
user on my system and also retired, making such a professional solution
going way too far.

I can be patient, but i would like to find the most reasonable path to
get a more up-to-date system soon. Would anyone with more experience,
than i have, give me their point-of-view/recommendations as
food-for-thought, please?

Thank you in advance
DdB


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