[crabbone]

My first "real" experience with Linux was with Wubi (Ubuntu packaged as a Windows program). I think it was based on Ubuntu version 6 or 8.

I also tried to update it, when the graphical shell displayed a message saying that update is available. Of course, it bricked the system.

I've switched from Ubuntu to Mint to Debian to Fedora to Arch to Manjaro for personal use and had to support a much wider variety of distributions professionally. My experience so far has been that upgrades inevitably damage the system. Most don't survive even a single upgrade. Arch-like systems survive several major package upgrades, but also start falling apart with time. Every few years enough problems accumulate that merit either a complete overhaul or just starting from scratch.

With this lesson learned, I don't try to work with backups for my own systems. When the inevitable happens, I try to push forward to the next iteration, and if some things to be lost, then so be it. To complement this, I try to make the personal data as small and as simple to replicate and to modify moving forward as possible. I.e. I would rule against using filesystem snapshots in favor of storing the file contents. I wouldn't use symbolic links (in that kind of data) because they can either break or not be supported in the archive tool. I wouldn't rely on file ownership or permissions (god forbid ACLs!) Try to remove as much of a "formatting" information as possible... so I end up with either text files or images.

This is not to discourage someone from building automated systems that can preserve much richer assembly of data. And for some data my approach would simply be impossible due to requirements. But, on a personal level... I think it's less of a software problem and more of a strategy about how not to accumulate data that's easy to lose.