Comment Re:Yes, and yes. (Score 1) 1100
1. i've been using ubuntu since 6.06 and that (the grub menu getting bricked) never happened to me), neither by clicking on the orange icon nor by a command-line 'apt-get dist-upgrade'
it didn't fail once in any of my three ubuntu boxes or my two debian boxes (the automatic menu.lst update worked flawlessly for me since debian 3.1)
2. the menu.lst file has special commented sections to add all the customizations you want which will be added automatically to all kernel options when you run grub-update (i have set the text mode consoles on my main debian box with framebuffer video this way, and never lost the config. in any kernel upgrade)
i think you were a victim of a very broken installation (missing or corrupted files maybe?)...