Can you open specifications from Sample data? I wonder if the data extension of the live data has had an application association already made through Windows.

I'm assuming that this new workstation can create and save specifications OK - that being the case can the other machines open specs created from the 2000 machine?

Because other machines are OK, then that implies the specs you are trying to load are OK, and the issue lies with the new machine. There are settings saved to the spec (such as Printer Driver). Does the 2000 machine have the save drivers (names) defined?