I had similar experiences few years ago as well. I realized (after the fact though) that patience has its own rewards. The next time something similar happened i.e. either data corruption (which grub and others come into), and borked/broken package update. In both the cases I asked around foras, pored over web-pages and had 4-5 different solutions to the problem. With Debian, it always pays to be like calm water instead of being turbulent water.

Backups though important are tedious and only helpful if something goes wrong. If you are going to make a habit of it, then go for incremental backup solutions.