When they're raising with any damn thing
I did really well, two of the nits went busted, the other two made no progress, and the two wild and crazy guys went busted and left. I left shortly after.
One of the reasons I did well was that I got lucky. One of the reasons that none of the nits did well was that none of them knew how to adapt to players who raised or called raises with about half their hands (which is what the wild and crazy guys were doing).
For example, one of the nits frequently would limp in (he was in front of the wild and crazy pair) then fold to a $10 raise from wild and crazy guy. Later he told me that he was folding hands like KJo in that position.
The wild and crazy guy was making those raises with at best hands like 98o and better. That's about 44% of his hands. He may have sometimes been raising with worse hands. Against that range the KJo is a 53% favorite.
At the same time he was folding hands like KJo to a raise I was calling those raises cold with ands like K5s. With that hand I was a dog to the raising range, by 45/55, but the wild and crazy guy had a terrible bet tell (he bet small when on a draw and bet big when he flopped a hand) so it was easy to play with him after the flop.
Adapt. If they want to gamble then get in their and gamble with them.