Hi M., I've been puttering around the house trying to come up with a diplomatic way to respond to your post.
Okay, so I totally know where you're coming from. It completely sucks for moms when their kids experience disappointment. Just breaks your heart, you know?
But, I don't think taking steps to control their environment to such a degree that they don't HAVE disappointments serves them well.
In fact, I feel this is the current generation of parents' Epic Fail (every generation has one). I love the 1970s movement where it started being popular to raise your kid in a more cerebral way, rather than beating them to a pulp to achieve the same result. But now it seems parenting styles have gone off the other extreme.
I mean, the whole Every Kid Gets A Trophy philosophy does not sit well with me. If we were all the same, society would cease to function. It's also an affront to individuality.
Lookit, I absolutely remember being in school myself while such PTA programs like the one you mentioned were all the rage. I was not a popular kid either. However, I don't remember taking it as an attack on myself when someone else got something I didn't. It actually gave me the opportunity to be big, to be above it, to be comfortable with my own value as a person in spite of this (perceived) suggestion otherwise.
I also remember my own kids' disappointments very well, and yuck, I hate that. Nobody LIKES it. Here's what I think I did:
Instead of trying to end/change the thing they find disappointing, upsetting, unfair, etc., I probably said something like this to them (using the example you gave where they did not get a candy gram when another kid did):
Really? I'm surprised. I would think you'd be happy for them (kid who got candy gram), after all you have (list all the wonderful things they have in their lives, or a specific example of some awesome thing that recently happened to them) and they don't.
Not sure if I'm making any sense here. The quote "prepare the child for the path, not the path for the child" comes to mind.
In fact, I think personal growth stems largely from disappointments, perceived unfairness. I think when we deliberately shield our kids from everyday reaction to the real world around them, we rob them the chance to gain substance. Or something.
I think I have tried to make my message to my kids, on this subject, this: Sure, everyone is special, but none of us is special in exactly the same way.
Good stuff other people get/have, does not take away from the good stuff WE get/have. See?
Anyway. In this EXACT situation, here's what I did with my kids. I sent them in with money to send OTHER kids candy, because it feels REALLY good to make someone else happy, and for that they should feel really good about themselves. And they did. And they do.
So maybe you could view this as a chance for your kids to GIVE, rather than the possibility your kids might be disappointed.
Sorry about the book.
:)