I actually had a similar upgrade to do that I've been postponing for too long. I ended up rebuilding all functionality on the server on a different server -- th

I actually had a similar upgrade to do that I've been postponing for too long. I ended up rebuilding all functionality on the server on a different server -- this time also creating the necessary automation for both provisioning and migrating, so I can rebuild it much cheaper next time. Did it take longer than slogging through a dist-upgrade? Probably. Does it cause some more inconvenience for users, like changed host keys and upgrades of software that might not have needed upgrades? Yup, definitely. Does it let me sleep well at night knowing I'm no longer dependent on a specific machine staying un-broken in the near future? Sure as hell. ---- (I also ended up splitting apart the independent functions the machine provides onto multiple machines, one for each purpose. This increases my exposure to machine failure, but simultaneously limits the blast radius. That's a good trade-off, for the most part.)