How would the dealer know the "right amount" of chips? You must be talking about a limit game, when there is no such thing as a string bet. Once you say raise, everyone knows the exact amount of your raise, so you can make multiple trips putting it in.
As for your friend, again, this sounds like it must be a limit game. I wouldn't tolerate it if I was the dealer or floorperson, but technically what he is doing is ok. He hasn't announced raise, and he's simply doing a "bad job" of stacking out his call. He fumbles around with his chips and then either pulls some back or leaves them there. But again, this only "works" because you are talking about a limit game. And..... if it's $2 to call, the second he releases $4 from his hand, that should be a raise. You can't drop 4 chips and then pick 2 back up. You can have 10 in your hand and drop 2 and then drop two more on top of them or next to them, but as soon as you do, they need to stay in the pot. You can't pick them back up again.
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