I haven't had these kind of upgrade problems since updgrading from 7 to 8. Did you really have trouble upgrading to, e.g. 10.04?
It seems to me that there's some problem with your HW configuration (WiFi etc. - never had problems). Did you consider staying on some LTS. I've found 10.04 to be extremely smooth. If you don't want to have the trouble, just stay on LTS :).
I did. (9.10 to 10.04) I lost my graphics driver during the update and when I fixed it my sound card went for a toss. But a clean install of 10.04 solved the problems, so I don't understand why the upgrade can't work without problems.
It seems to me that there's some problem with your HW configuration (WiFi etc. - never had problems). Did you consider staying on some LTS. I've found 10.04 to be extremely smooth. If you don't want to have the trouble, just stay on LTS :).