Re: 500BB pot vs maniac
Playing middle pair, crap kicker 250 BBs deep versus a maniac is not my favorite thing, which is why I would probably fold preflop.
Meanwhile, though, if that sample hand is Villain's typical approach -- and it sounds like it is -- then I don't think position matters that much. I would just prefer to have better high-card strength. If I played, it would probably be with the idea of letting Villain steal the pot from me unless I hit the flop really well (as in at least top pair). Which probably isn't really the way to play against this guy (and it certainly isn't if the stacks were shorter), which is why I wouldn't bother with T8s from the SB when this deep. (But I probably would play the same hand vs. a min-raise if I were in the BB and knew I was going to be HU, so I guess maybe I'm being a little picky.)
But once you play and flop top two, it seems like it's time to play for stacks. Villain isn't going to let you play for much less, and you got your rare monster on the flop.
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