Thanks for the responses, all. It looks like the general consensus is "go for it," so, as Sting once put it, consider me gone. Now to find a chunk of time to archive all accumulated kibble to some CDRs and actually DO the job. And download all the drivers. And so forth, and so on.
I may have to check some of the Medieval: Total War forums as well. Maybe an upgrade to 2000 will fix the annoying sound issues during battles (I want the crunch of mangonel stones hitting their targets, not the sound of breaking glass)...