My mother is like the guy you mentioned, and the rest of my family slightly less so (one of my brothers even plays the odd game or two.) I've never run Vista, but I did like Windows 7 (for general use) and Windows XP (for running old DOS games.) That being said, I found a program that works almost exactly like Paint (it's missing the "Paste From" command, although it'd be fine for making Paint chibis, sprites, or pixel art), although it costs $10 to get the full version (damn Mac trying to squeeze every penny out of me.)
No need to worry about me, my compy should be out of the shop soon and then things should be good. Also, no rush for the art; your well-being is much more important. I hope everything's going OK in your personal life now, and if I can help with that in any way all you need to do is ask.