On the flagging issue, it seems that a big part of the problem is a mismatch between the intent of the developers (who see voting as a tuning mechanism for the value of a particular post) and users (who perceive it as a reflection on the esteem of the post's author, which it sort-of is because it is also tied into the reputation score).

Now on one hand, "the customer is always right." and maybe the developers should learn to understand the flag the way it's perceived and used by their customers, instead of how they'd like it to be perceived.

But on the other hand, I wonder if the two perspectives might come into harmony by changing the nomenclature from "upvote" and "downvote" to something like "add value" and "reduce value", or even change the check boxes into a value adjustment dial. Then, the guidance message could be, "I think this post should be worth more," and "I think this post is worth too much." Maybe that sort of guidance would ease some of the sting of the flag - errr - value reduction?