Its an interesting question and there are some really terrific responses above.
I'm not really sure how to answer it other than both our boys both exceeded and fell short of both their's and our "hopes" at different times. I'm not sure I'd have called them expectations - more like "hopes."
They both had tough, tough days...weeks...months...seasons. And they both have had terrific days...weeks...months...seasons too. Playing off a theme mentioned in different ways above - they sure did have to grow up in more than one way and (at times) it was tough to stand back and just let that happen as a parent. I think perhaps the most rewarding part for us were the times they learned how to pick themselves up off the dirt and go back at it and make 'a new plan' as Coach May says.
As I said...tough to do sometimes. But very rewarding when you see your son grow into a man.
Good topic. Hope to read more responses.