Having to replace working equipment because the software that you paid for can't be transferred to a new computer is a nightmare Often, the old equipment works just fine because the laws of physics haven't changed.
But equally often, by the time it's that old, it's being used for a tiny subset of its original, perhaps for exactly one repetitive procedure. In those cases, it's often easy to whip up a little Python program that talks to the RS232 port via a USB-RS232 converter.
Will the Python program last any longer? Maybe not, but at least its source code is in text format.