Re: Raise him now or raise him later
 

I think 5 betting this preflop gives the villian the opportunity to get away from his hand too easily. Given your positions the villian in this situation may think that you are trying to isolate his steal raise but once you 5 bet he knows you have something legit.

Raising the flop in most cases is probably the best play since it gives you the best chance to make the most money on the hand. This is particularly true against aggressive opponents. Since there are two diamonds on board the villian may think you are pushing a draw and play back at you. He may also slow down on the turn once a third diamond hits.

Make this a rainbow board and a tight less aggressive player and I would consider waiting until the turn to raise. However, if this player is weak and capable of making big laydowns I would just play it straightforward and raise the flop.

Re: Raise him now or raise him later
 

Like pre... RAISE flop

Re: Raise him now or raise him later
 

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imo PF is fine. players' ranges of 5-betting hands is way too narrow and results in collect much fewer bets postflop (e.g. c/c all 3 streets by scared villain).

flop raise is a must 100%. you can raise the ragged flop and possibly 4-bet.

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Great advice. The 5 bet would have defined your hand too well and killed your action, unless he flopped a monster. With the board here, raise flop & turn for sure. If he b/3b then just slow down but take it to showdown regardless.