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"Name one piece of hardware that's CONSIDERABLY easier to install on a Mac than on Windows?"
"My roommate in college had a Mac, and I have to say that Mac OS X is probably the most brittle, crashiest *NIX I've ever seen."
Thats funny, its never crashed on me and has been nothing but totally rock solid. Sounds like the problem is with your friend's computing ability (or rather... lack theirof)
"I can recall several instances where I had to go to drop to the command line for him, just to delete some files off his desktop. The GUI wouldn't let him.
I think you're lying. I've never heard of such an error.