His story reminded me a lot of the time I switched from Linux to OS X. There was a point where compiling my own kernels stopped being fun and I just wanted a computer that I could work with instead of work on.
Why did you have to leave Linux? You could have just stopped compiling your own kernels. Even the guys who tweak and compile the kernels we deploy to our servers just run stock kernels on their desktop machines. Sounds like you have the same hacker OCD that makes this guy overclock his processor and install third party ROMs and then have the balls to complain about stability. (He makes it sound like the modifications were necessary to make the phone work in the first place, but overclocking the processor falls into the "I just can't help myself" category and undermines his credibility a bit.)
"Compiling my own kernel" is often a metaphor for the effort involved in running a Linux system. I run a dual-boot Windows/Ubuntu system right next to my MacBook using SynergyKM to control both, so I have a good opportunity to compare both on a daily basis. The "compile my own kernel" factor with recent distributions of Ubuntu (9.10 and newer) is really, really insignificant.
So, it's a mixed bag. "Linux" means so many things that it's hard to say "Linux is easy to use" or "Linux is hard to use" and not be right in both cases.
No, I had to compile my own kernels for several reasons.
1. My soundcard didn't work with any vanilla kernel (+ modules)
2. I owned a webcam that had a slightly different USB id than the ones supported by the driver that in fact also supported mine.
3. I owned a laptop with a touchscreen which involved having to compile some non-standard modules.
Anyways, things have gotten a lot better since I've "left", but Linux (on the desktop and Android, for that matter) will always be "very good the next release". Which is, of course, utter bull. If you don't have excellent polish as a priority from the start, you'll always be fixing things for the "next" version while simultaneously introducing 10 new half-baked "features".
Once a hacker, always a hacker. For some people knowing the ways you can tweak something makes it quite hard to stop yourself doing it. Sure, he could dump Ubuntu on his computer, but he knows how to poke around and change the settings to get his money's worth from his hardware. That knowledge won't transfer to OSX, and (hopefully) nor will that temptation.
It's your choice to compile a kernel. You could also have just used a distro like ubuntu. I think for a hacker, the difficult part here is to forget about all those tweaks that are possible.