Is that the healthcare-related
labmate? It looks like it has no trouble running under modern OSes,
even Win7. It probably even runs under Wine in linux. The description says nothing of particular printer requirements.
If that's the only computer and printer he has, then I understand the dilemma. Otherwise, try it on winxp or something recent, and any inkjet or laser you can dig up. Whatever his newer computer(s) have, it'll probably work.
The "it's not gonna happen" response to Brad worries me a bit, considering how much time you and your dad have probably put into this already, and how much more time it will require to get up to speed on such ancient hardware (and with no internet connection, a simple thing like getting the right printer drivers if it needs them will be very painful).