Well, the issue I ran into was that, if the monsters could focus all their attacks on one target or split attacks to multiple targets, focusing all on one would almost always be the better choice, and I wanted to avoid that with the new system, hence only allowing one grapple per target per round.<br/><br/>Though, that was with them getting large bonuses to the grapple check if they focused on one, in addition to having more tentacles to do stuff with, so that might not be an issue...<br/><br/>Hm, so here's what I'm thinking: monsters can usually make multiple attacks per round.  They can substitute any number of those attacks for grapple attempts, even if they're already grappling a character.  For maintaining a grapple, only one of those checks needs to succeed in order to maintain; further successes allow the monster to take additional actions with the victim.  A monster cannot pin a character in the same round as they are grappled, however.<br/><br/>Due to the sheer number of appendages a monster has, pinned characters will have difficulty escaping.  A successful escape attempt only causes the victim to be grappled, instead of completely escaping.  Further, a failed check by the monster to maintain a grapple on a pinned character also only reduces the character's condition to grappled.  A character's allies can assist in freeing her by making a Sunder attempt on the tentacles (normally, hardness of 0 and HP equal to the monster's HD); a success deals damage to the monster equal to its HD and moves a character one step closer to escape, from pinned to grappled or from grappled to free.