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Push preflop the second time it comes to you after looking at villian and saying "I knew you were gonna raise".

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I think playing for a set is more +EV than pushing preflop and making him fold. He might just call you with a coinfip. If you hit your set you're getting paid.

As the board fell I think you need to decide on the flop if you are going to call him down. Either fold on the flop or commit $200 to your 66 unimproved. I prefer a fold. If he has two overs you are flipping, and his betting pattern means nothing, so you aren't getting any information to put him on imporved trash versus unimproved trash. I think this play is only slightly +EV at best.

A better approach to this player is to wait for TPTK and raise flop, call reraise, call two more barrels.