Some very interesting and informative posts here since the last time I looked in - particularly from Vancouv - who seems to have much relevant experience.
In addition to my previous offering, I'd like to say that I'm not overly worried about something being "old" per se - especially as I'm not that young any more myself, yet still work reasonably well. The problems with computer systems usually occur when some guy has "fiddled" with it! Updates, mods and improvements often turn out to be nothing of the kind - whereas the original version may very well have carried on doing what it was designed to do.
Obviously, advances in technology have enforced some changes with older languages and versions not being able to run on modern platforms - though introducing these and debugging must be the stuff of nightmares!
Not to mention having ones start-up files fragged after the last use and sitting there ready to corrupt.