I actually did that. Or well, I was planning to upgrade the Debian version and instead of doing it in place I replaced the drive (kept the old around for a while just in case) and did a clean install. I didn’t make any new backups or moved configs or anything outside what I already had, the system was back to operations faily quickly. The main reason, I have a markdown file describing every configuration and recovery step needed to get a fresh system to a fully working state in case of a disaster, and my test showed that it worked great. It does take a bit of effort to keep it up-to-date, but as shown, really worth it, and it douples as a small wiki for accumulated knowledge. I do wish to play with Ansible at some point if I have the time, but this works for now.