Rate my play

[that_pope]

So you know the getting chips ready to call means weak, so why did you check? Were you trying to go a level above him, he knows he is showing weakness, and you checking means you are even weaker than expected, which gets him to bluff?

I would really like your thinking on hand 1, as it is player dependent. Is this the type who can show weakness by intimidating with calling chips, and then pulls off a check raise??? (I have never seen this personally, but am sure it exists...)