[KurtSF]

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Hero raises to $150

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I found your problem.

The reason this is bad is because you are committing a substantial portion of your stack to a pot that is going to be huge. You don't leave yourself options.

If you want to see the flop, just call the $50. The pot will probably be about $200 and if you like the flop you can crai, of just c/f if the board sucks.

The higher variance play, but probably more +EV, is to push your edge preflop. Hand values are exaggerated in straddled pots; you're holding a monster. Just shove. If someone's got AA or KK, meh too bad. But you'll get a lot of calls when 88 convinces himself you're making a move with Ax and when Ax convinces himself you're making a move with 88, so there is a lot of upside to counter the (few) times you're dominated.

As played? I can't see a real advantage to either c/fing or open shoving. If you shove you're toast if you're called, but putting $350 into the $465 pot you only have to get folds about 40% of the time for this to work. c/fing is obviously 0EV and I'd say shoving is within spitting distance of 0EV also. So flip a coin, or better yet, make you decision based on what you want your image to be for the next hour or two.