In the hand where Diceman has 65o in the 58692 board Skates says something like this: when vilan has 8x and we bet big in the flop, we induce him to check/raise us all-in, whic is a very good play. But when he has big overcards and we bet small and we know that he might bluff a lot in the river, it can also be a very good play. My question is, how can we decide wich of these two options is the best one as we don't know what is his range in the flop.Thanks a lot
It's going to be very opponent-dependent and be based a lot on how they interpret your sizings and river bluffing frequency with weaker sizings. In general, that's a board where you shouldn't be betting small on as a standard.