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Ok, so how did the switch really go?
I didn't go on vacation just after pushing the change of course ;)
Testing went quite well. We only found one custom daemon that was still storing too much data in /var/run, which had become a small tmpfs, and failing (/var/run used to be part of the root filesystem). It was rebuilt to store data where it was supposed to.
Most of the time was actually spent helping our package owners convert their RPMs to debs and switching to new upload and review mechanisms.
We also wrote new review tools to diff and review our new image, built from scratch each time.