Well I finally blew away and reinstalled Ubuntu from scratch and I am now a much happier camper. I had done an upgrade from 7.10 -> 8.04 alpha -> 8.04 final release and my video driver was not in a happy place (could not use the restricted driver at all and any attempt to enable it resulted in debugging pain). Today I burned the Ubuntu ISO onto a disc and installed over my Ubuntu partition. The install went relatively quickly and hassle free.
And best of all everything just plain works! Huzzah!
I then proceeded to follow this guide for getting some of the non-default features:
I’ve heard of some relatively recent good developments on the Wine & Oblivion front so that may be an exercise left for the near future. (And if that exercise messes up the OS, I at least know its pretty quick and easy to get back to a stable system)