I've been using Debian since before woody, and am well aware of the usual caution against jumping versions. I have jumped versions in the past with very little pain despite it being officially unsupported. Obviously this time I gambled and lost as it clearly breaks your system more severely than usual.

None of that changes the user-experience comparison with mainstream OS's or parent's point about Linux's "‘stability vulnerabilities’ where the user has to tread carefully". Linux is well known for being a sharp tool without safety guards. That, and the "RTFM" tone of the typical response to trouble, are some reasons why the Year Of The Linux Desktop is perpetually stuck somewhere in the future.

The fact you can fix anything (even a misguided attempt) in 15mins with a live drive is a great strength imho. Back in the 90s you’d often have to reformat partitions to recover any OS.