I think you're correct that Apple is going to have to do things differently get some of their web properties to catch on, but I disagree heavily on your premise. For a counterexample, Facebook is professional-looking and very structured compared to MySpace, which in turn is very amateurish-feeling. There isn't any question which is preferred. Forums are amateurish. Stackoverflow is professional. I know where I'm goin…
My point wasn't that less professional looking websites succeed over more professional looking sites. It's Apple's focus on professional content (the select few) vs amateur content (all of us). I didn't mean to use amateur in a derogative sense. Amateurs are just people who don't get paid for their work. Re: Facebook/MySpace, I think this was a different dynamic. The thing facebook did right was tone down the design…
Besides that your point is not true I fail to see how it applies to Apple. Should they remake apple.com to something horribly amateurish, and then they somehow succeed? Are they failing?
And I bet that if some website which looks amateur succeeds over more professionally done the looks is not the key to success.