Regarding Redguard. I am playing it with no problem using DGVoodoo. So give that wrapper a try: http://dege.freeweb.hu/
I also have Arena, Daggerfall, Battlespire, Redguard, Morrowind and Oblivion,all with all their expansions. All original boxes and manuals and maps, etc, all sitting proudly onmy shelf and all on my PC on various drives! A little know reason to get Redguard if you haven't got it, is the 'Pocket Guide to the Empire' that's included. It's the definitive guide to Tamriel and it's people's and there has been nothing like it before or since!