I bought two Macs in 1984 and, while using other platforms, have stayed with the Mac owning several dozen personally. System 7, not merely lousy management, was a disaster for the Mac.
All the fumbling around with new OS systems, not just the lousy management, all but killed the Mac. Steve Jobs, whom I dislike personally, is correctly credited by Derrick Story as saving the corporation.
I viewed OS X with great apprehensive from its first announcement. I spent about 100 hours with the public beta and hated it about 90% of the time. 10.0.0 was a grave disappointment.
I played with 10.0.x off and on, mostly surfing, and learned to love that Quartz engine, but hated the slowness and interface in general.
10.1 shipped. Magic. Speed. GUI was starting to shape up. I've been 95% OS X since, the other 5% being digital photo touchup with Photoshop under Classic. Can't seem to find any Classic app of consequence that doesn't run fine.
From hate/dislike -> loving it. I dislike the rare occasions when I boot into OS9/Classic. The OS and interface I loved for 17 years is history for me.
The number of shareware and freeware apps is incredible. GoLive 6 showed up in mail yesterday. Have used Office X since it shipped. All of Apple's "i" apps + stalwarts like QuickTime are nothing less than fantastic with OS X. The list goes on.....
I found OS X both difficult and frustrating to learn. Too many old habits. And contrary to popular belief I believe the GUI will be more difficult for new users than Classic.
Bottom line: it's worth it. This OS X is fantastic and I'm not looking back. I'm launching Terminal and picking up "recipes" to type in to do odd jobs. Have several freeware "Terminal Manuals" from around the web. I'm working on geekdom. Doubt it will come soon. But in the meantime I've got 95% of my apps and better and newer ones keep being introduced almost daily.
Life is good.