Mark CMG
Creative Mountain Games
The issue is that the more resolution points you have, the more likely it is for a player to roll badly, and since the maneuver requires all of them to succeed for the player to accomplish their narrative desires, it makes the likelihood of overall success that much lower.
First, the narrative in this case would have been introduced by the player. Second, the tougher it is to succeed, the more pleasure that is derived from the accomplishment.
Keep in mind, while simulationism is one design goal, you also need to design to player psychology. If the designer wants players to attempt maneuvers frequently, it's important that A. resolving maneuvers is straightforward and quick to resolve (because if it's too complicated and takes too long to resolve, players and DMs will find it annoying to adjudicate), and B. players have a good chance to succeed.
Naw. Two rolls isn't egregious. The benefit of sliding under the table might be to avoid missile fire from the balcony, for example. The benefit of grabbing the leg as the PC slides through might be to keep the sliding DC lower. Players will always do cool things and can do many more cool things if the game isn't bogged down in restrictive mechanics and cumbersome resolutions. A DM might even suggest that sliding under the table is fairly simple, maybe a DC 10 ("add your Dex mod") but that stopping at exactly the point where the player can stab upward on the opponent would more difficult at maybe a DC 15. The player might even negotiate the situation asking if he could grab a leg when sliding through to ensure stopping in the right place, and the DM might respond that it would lower the slide DC to 8 but require an opposed Dex check for the grab. The player might think that the opposed Dex check should be easy because his opponent is a lumbering oaf and the DM might even suggest that an additional plus two mod might be warranted because the opponent might not see it coming. Of course this all happens swiftly and even more so in a game where the players trust the DM to adjudicate fairly. A trusted DM is always going to try and give the player the best chance to succeed and even make suggestions toward those ends.
The better DMs among us have also likely noted that a static DC check followed by an opposed DC check followed by a to hit roll is an example of building dramatic tension during gameplay by the rule of three. The better DMs would also be sympathetic to the player who tried cool things and probably utilize a bad roll as a chance to reward the player anyway or add in another game element. Perhaps the slide goes well but the grab is missed horribly. The DM might describe it somewhat comically but end the description by throwing the player a bone.
"You slide under the table well enough but completely miss grabbing your opponent's leg. He, on the other hand, is completely oblivious to you as you slide past him and onward under the next table along. Huddled there you find what appears to be a rich merchant and a young girl. He shoves a small bag of coins into your hand and says, 'Help my niece and I get out of this tavern alive and there's more where that came from.' You noticed the girl winced when he claimed she was his niece."
You don't encourage players trying cool things but simply making them easier. That actually just lessens how cool they are. You encourage that type of play by keeping the players engaged and knowing that even in failure some opportunities are to be had.
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