I think this is an excellent game and would probably keep playing a version that had some of the bugs worked out. The glitching through walls can be fairly infuriating if you have the ball completely enclosed and it gets its way out, plus the interactions with the edges of the screen can really screw you up (e.g. when you're drawing a line and you accidentally brush against the edge, so it drops the line immediately). I'd also get rid of the clickable stuff at the top left or reduce the play area so that stuff isn't in the way, since a couple of times I accidentally surrendered while I was trying to draw a line there.
One other improvement I could think of is doing a little forward calculation on your randomly-chosen initial state to prevent it from setting up scenarios that really are impossible or just no fun. Having the ball appear for a 10th of a second and then bounce off the top of the screen never to be seen again (because it went to the side) is no fun. Oh, and maybe stick a red dot or something at the top border of the screen when the ball is up there so you can track where it is horizontally. Oh, I'm full of suggestions.
Edit: how did the double mango pudding turn out? :)
XP doesn't have the "tall" start button and icons-only taskbar, and 8+ doesn't have Windows Classic.