I've had problems on my M275 from 8.04 all the way back. There were shutdown issues (won't fully shut down until I press power), startup issues (takes 1 full day to start up), and many more.
I have hit-and-miss chances when it comes to installing Ubuntu (I've tried installing it into this computer for a long time now). At the end, Ubuntu 8.10 (Intrepid Ibex) worked out the best. There were no startup or shutdown issues. The only problem I am facing is the use of video playback while I have Compiz Fusion (Advanced Desktop Effects) running. The video card is fairly old, and didn't work so well in Windows anyways, so every time I want to playback video I just turn off my desktop effects.
For your Windows problems, the laptop actually ships with Windows XP Tablet PC Edition (which I suspect is XP Pro with some extra tablet features). I'm not sure whether that would be the cause of all your tablet issues. I have the original driver CD's that's shipped with my (two) M275's, both for the Tablet PC Edition.