You never want to under-estimate an opponent - you only have to drop a piece to lose to someone 300 or 400 points lower. That being said, I don't minemind playing weakies and getting an easy kill because the next round... I'm probably going to be the weakie. So it all comes out in the wash.
I have to admit I experiment on C players. Not to see what I can get away with as such, but to try new things, be uncommonly aggressive, or sac a piece when it would be fatal to do so against a peer. I have nearly been up-ended more than once, of course, but that's the risk and frankly half the fun.