Andrew Cunningham tried to work with Mac OS 9 and published an interesting account of his experience at Ars Technica. Make sure to reach the conclusion for some good points about software updates:

People love to complain about change. Those complaints aren’t always unwarranted. We live in an era of constant updates, where your browser changes every six weeks, and your operating system changes every 12 months. Who even knows how often they’re changing Gmail and Twitter and Facebook? The idea of supporting and using a single OS for 13 years seems completely absurd. Sometimes you just want everything to stand still for, like, a second.

Also, don’t miss Riccardo Mori’s counterpoints at System Folder.