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Before you talk about obsolescence, look at the world of emulators. You can get an Apple II, Atari 400/800, Atari St, and Amiga emulators. Not to mention C/PM emulators and there was the old Virtual PC 2004 emulator (y'all may remember my problems getting it to work on my new machine.) that will let you run any non-DRM'ed Microsoft OS based software that dates back all the way to DOS 1.0... Oops, and I forgot MAME, which emulates arcade games, and Atari 2600 emulators...
With A full set of emulators, you can run just about anything that wasn't DRM'ed. (Leaving the modern Mac world out of it, of course...)
And fully backed up...of course!
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