But you do have to set correct expectations, significantly "It's not actually Windows." Meaning that some actions need to be looked at with fresh thinking, not Microsoft thinking.

For those still on '95, '98 or 'ME (or even W2k), Ubuntu is actually a good upgrade, because it's different enough in very roughly the same ways as XP or Vista is. That's one reason I took my Dad from '95 to Ubuntu. If they later encounter XP or Vista, they will have an apreciation of the "Microsoft-ness" of them and all that that entails.

Wade.