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Check out this extensive overview of Microsoft Bob: it even traces Bob's influence up to Windows XP and Messenger. Along with oodles of other software obituaries, there's a lengthy discussion on the usefulness of supposedly "obsolete" software, e.g.:

Let's look at it another way. If you could do everything you needed to with a version of a Windows 95-based "office" suite, and you could purchase the original software at a thrift store for, say, US$5.00, would you do this or would you spend upwards of $700 for the newest version of the same software?

If you knew you could accomplish 99% of your computing needs on a 586-class PC, and you could get the system for free, would you still go out and spend upwards of $1,200 on the "latest and greatest" system?

Which is a good point...the only problem being document compatablity: if you're running Word 97, and a client sends you a Word 2003 document, you're up shit's creek. Maybe if there was a backwards conversion utility, you could get around that. Or -- shocker! -- maybe you could just not use Word.