Yeah, it was tempting. The first twenty times or so, I was literally laughing. I should have plugged in my mic, just so the guy would notice that his habit is visible to everyone. At first it seemed endearing, like the way a puppy chases its own tail. After thirty or so check... check... checks, I was a little frustrated. I did press UP on the d-pad and mashed B Button to try and whistle or make a verbal taunt.
I was wondering how they would implement the gambling, but in the end it is like FFA and Gang Games: they instance a new "free roam" with the needed context, building and rule modifications, objects, whatever, and turn the players loose. The players are free to do whatever within the context of the current settings, and gambling is identical to the single-player experience excepting that there are no "Skip to Your Turn" or "Quit" options (you can leave the session via the Back Button as usual).
In as much as that, I'd been worried that they'd keep the players in the same Free Roam in which it was initiated, which would allow some wannabe Public Enemy to just enter saloons and interrupt games by killing everyone. The instanced world prevents that, of course.
The other thing which is interesting is the Liar's Dice and Poker are "modes," like FFA and Gang Games. You can join them via the online menu, or you can start one for the current Free Roam's players. It also cycles through a playlist for each of the locations where you can play the game, which struck me as a funny way to add variation: Liars Dice in THIEVES LANDING. Up next: Hay mucho Liars Dice en Escalera!