I think Python works on fairly antique hardware, whatever OS you use (as long as the OS works ok). You can get a DOS version of Python 2.2 at http://www.caddit.net/ , but I don't have any good suggestions for a UI then. This might work after some tweaking: http://www.effbot.org/zone/console-index.htm
If you google for "python curses" you'll find info on that route, and if you go for a GUI solution on Windows or Linux, there are more routes than Tkinter. I'm not sure what to suggest on really old hardware though. Perhaps pyFLTK or FxPy are lighter than the typical alternatives. See also http://wiki.python.org/moin/GuiProgramming Unless we're talking about several installations, getting at least a Pentium III is obviously much cheaper than to spend several hours getting the program to work. For a dirt cheap system with several users, curses and terminals with a linux server is obviously hard to beat. A slightly more modern approach would be a web based app. -- http://mail.python.org/mailman/listinfo/python-list