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" (And he's conveniently forgetting the other costs of those old systems: learning assembly, having non-portable code, runnable only by geeks, etc.)"
Is it really that much better: learning insanely complex APIs, optimizing/adapting for updated versions of components and layers, runnable only by geeks.
Yes, Windows machines are only runnable by geeks. Before you disagree just consider how much malware is on the average machine. Same with unix-variants except perhaps OS X. At least my mom gets by with that.
That said I have AmigaOS 4 running on AmigaOne here. It's far faster than any other machine I've tried and it gets the job done. No, it's not ready for the consumer market, but I'm sure as hell having more fun with it than any other OS.