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I actually switched around 2 years ago now, but I can tell where he's coming from. I actually switched off of Windows to BeOS around 5 years ago, so my real migration was from Hacked-to-be-modern BeOS R5 to brand-freaking-new OS X 10.0. I think my BeOS experience prepared me well for having large parts of the OS missing or non-functioning. When my machine first arrived, I still had to boot in to OS 9 to burn a CD or DVD, install drivers and that sort of thing. OS X wasn't even the default bootup. About 3 months after buying my Mac, I was getting very discouraged. I had purchased it to run OS X, not OS 9, and stability in either was terrible. A switch back to BeOS, Linux, or even Windows seemed inevitable.
Luckily, 10.1 came out right about this time. I was very pleasantly surprised to discover its upgrade price (nothing), but my hopes for the platform were lower at this point. 10.1 really got me back into it. I could finally do stuff I had wanted to do, like making DVDs and running (more) Unixy stuff. The development tools had become useable (though still not great), and the apps I really wanted (Office, PhotoShop, DVD SP) really started arriving. 10.1 was enough of an upgrade that I was willing to stick with my Mac for a while longer.
After a year of Mac owership, it came time to buy a computer; I try to update every 12 months. I don't know what had happened in those past 12 months, but there was no question in my mind at this point that I'd be buying another Mac. I finally felt like I was part of a computing community where stuff really happened. I had switched to BeOS because I was upset with Microsoft's apparent inability to make neccessary changes, only to end up with a dead OS. In Mac land, stuff really happens. I couldn't turn my back on this.
In the next few months, I plan to buy a new G5. I'm reasonably confident that it will be at least as useful to me as my previous machines. 10.3 looks exciting, and I've become completely hooked on iTunes and its store. In the end, my Mac turned out to be all I had wished for, it just took a few point releases.