They have these types of stations at Paramount parks (we saw one last summer at Canada's Wonderland) and thought they were a great idea. Saves so much time over measuring at each ride when they are "close".
Mainebound, you bring up something that I have seen a lot of over the past few years-platform shoes, putting a girl's ponytail high up on their head, cowboy boots or shoes to raise the child up a couple of inches. I think that is a sad thing to do in order to give your child a couple of minutes of fun (not saying you did this Mainebound--just remarking on something you brought up).
I have always prepared my son ahead of time that he was not going to be able to ride certain rides and if he was close we would just tell him "probably not going to happen". If he was able to go on, then there was no disappointment. IMO it is not worth the chance you take for a few minutes of fun.
On our last trip to WDW I saw a smart CM at the entrance to something in AK (probably Kali) who was measuring a young girl and left her stick off the ground about an inch or so. The girl's shoes were like a platform sandal, she had the "Pebbles" type of ponytail on top of her head and her mom kept telling her to stand up straight or she wouldn't get to ride with the rest of the family and the "big kids". We were right behind them waiting to enter the line and thought it was sad. Thankfully the girl was not upset about not riding, I think her mom was more miffed than she was.
Anyway--sorry to go off on a tangent, but the rules are definitely there for a reason. I used to work for Six Flags when I was younger and can't imagine an under-sized person riding something made for someone larger or taller.
Now if only WDW would get those measurement booths, that would be great!