Apple's refusal to support FLAC, in favour of their own crappy rip-off (which they refuse to licence to 3rd parties) was, for me personally, the moment they jumped the shark. I feel later developments have borne this out.

I mean you can buy music from Metallica and The Beatles in FLAC format. If Metallica and The Beatles are out ahead of you on some aspect of digital music, it's time for a rethink.