Yeah, the Help action is great. The games I run I'll usually treat two players working together as using the Help action for the player with the better skill.
I'd be in more favor of this if the DC went up after every failure. e.g.:
first character gets a DC 15 check
second character gets a DC 17
third DC 19
fourth DC 21
It makes sense that a failed check would make subsequent checks more difficult. Similarly, this would open up systems where successive checks could be made easier through each character passing a check and really provide a sense of teamwork in convincing an NPC. However, this would require Larian to write and voice ~4x the amount of check-dependent dialogue, as I'd want the NPC to respond after each failed check.
Failing ^, I vote for max 2 tries or one at advantage, assuming another character speaks up to help. And of course we should be able to choose which character(s) respond.
+1 for a scaling DC
It totally makes sense for the amount of attempts to vary from NPC to NPC. (Some are resolute in their actions, others are on the fence, etc.).
I think that might be difficult to implement in the game though (As it would need to be set for each NPC). So, a scaling DC each attempt probably would be easier to code.
Failing ^, I vote for max 2 tries or one at advantage, assuming another character speaks up to help. And of course we should be able to choose which character(s) respond.
If this is how Larian implements multiple characters working together in the dialogue, I'd be happy with it.
