Shimiel's page

How about a compromise between the two camps?

Multiple creatures can attempt to grapple one target. The creature that first initiates the grapple is the only one that makes a check, with a +2 bonus for each creature that assists in the grapple (using the Aid Another action). Multiple creatures can also assist another creature in breaking free from a grapple, with each creature that assists (using the Aid Another action) granting a +2 bonus on the grappled creature's combat maneuver check.

Each attack that lands with the grab ability is essentially another limb trying to hold onto the target creature. How about instead of 4 grab attempts for that giant octopus, only do one grab attempt at the end of the attack routine that adds +2 for each extra grab attack that landed?

This way, you don't need to waste grab attacks, but it doesn't end up being a silly number of grapple attempts. I know each claw, tentacle, pincer, etc.. isn't its own creature, but it might make sense to resolve it that way in this case.

If you had enough of them, like that giant octopus, it could even make the -20 penalty for trying to not be grappled yourself more palatable.