Yes, AFAIK he's an Apple employee. I dealt with him briefly over an Apple TV issue back in the v1.0 firmware (the clock seemed eternally off by either 1 hour or 9 hours, and both my Apple TVs were different in that regard).
It's disappointing to hear that this is actually
expected behavior, since it really is counter-intuitive to the way everything else handles sorting. The omission of leading punctuation was probably intended to get tracks with names like "Weird Al" to sort correctly, and in many cases the leading punctuation really is
not part of the name (your ?uestlove example notwithstanding, of course
). Using the Sort Fields for those few exceptions probably isn't that big of a deal for most.
The only other option would have been to choose what punctuation
does get ignored -- a solution that would have probably created a different set of complaints, and a lot more issues for international versions.
On the other hand, numbers sorting at the bottom is definitely not normal or expected by any other sorting standard.