Boss wants me to program

[Magnus Lycka]

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.