As of this evening I've got the last thing configured that I really need to have... my WACOM tablet.
I've got my nVidia TwinView dual monitor system configured the way I like it, and using the settings found on
this webpage the Wacom fits in exactly as I want it to, with the tablet only active on my main monitor, while my normal trackball can still stretch across both displays.
Having done this, I've got to say that the end user setup experience still has an incredibly steep learning curve. There are no GUIs on these configurations, everything had to be manually typed into my xorg.conf file using gedit (notepad) all while granting myself root permissions via terminal to save the file.
This will never work for average end users. I've got nothing bad to say about Ubuntu, when it's working it's exactly what and how I want it. But working with configuration does make a point of just how well Microsoft has the average user covered.