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My concern here would be that that computer is going to give up the ghost at some point
I dunno... If the thing's been going strong since the early 90's, who's to say it won't just keep going? Heck, I'd even go so far as to say that it's now proven itself as a stable system, and anything else you replace it with might not have that kind of track record.
I agree that having a backup plan is a good idea: VMWare, WINE, or a terminal emulator, like you said. Would be nice to know which of those things *would* work if you needed them to.