I lead into the raiser sometimes (sometimes with air if I think the flop missed him, or he had a low to mid pp that didn't set) but usually only if I think that will cause him to fold (after all, I did the betting, he would assume I figured he would bet if checked to him, so why did he do that? then it would get him thinking maybe he wants me to raise him and if he don't have much of a hand, he won't feel as confident anymore).

During the 2+2 tourney, there was a hand I had where I had KQ, and was in the blind facing a late position raiser heads up. Flop came AK5 (or something of the like) and I bet into the raiser with my MPTK, he thought about it, then said right before folding (got my kicker beat?) and folded, and I showed him my hand.

I'd say it depends mostly on the player though on what the best line is. Good reads help out here, and sometimes aggressiveness wins pots, which is why having position is very important.