D&D General The Beautiful Mess of 5e

Absolutely. Pretty sure my newbie player doesn't really get why any of these exceptions occur, and even my more experienced players hit a wall sometimes. I had a fight with a monster that cast darkness and the cleric - an experienced player! - didn't quite get why guiding bolt had disadvantage when fired at the monster in the darkness while the bard's hideous laughter just couldn't target the monster in the darkness and their shatter had no problems forcing a saving throw. Grappling introduces similar ambiguity (and is distinct from Restrained!).

It'd be really nifty if the modularity of 5e included an easy way to simplify a lot of this for some of the less math-friendly players. I think 2014's Proficiency Die has some legs on making it more distinct, but still...lots of overhead.
I actually love the proficiency die. I Pooh-poohed it back when it first appeared in the D&D Next playtest, because I didn’t like that the random nature of the bonus meant I couldn’t figure out, say, “I have +9 with thieves’ tools, so I can’t fail to pick a DC 10 lock.” But, I was wrong. The value of that knowledge is relatively small, and for some reason adding the results of two die rolls and one flat bonus together is easier for a lot of players than adding the result of one die roll and two flat bonuses together. Plus, it makes the way the proficiency actually functions much more transparent to the players.
 

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Plus, it makes the way the proficiency actually functions much more transparent to the players.
Could you clarify how you think the die makes it more clear to the the players? I've been toying with the idea of changing to prof. die, but I just didn't see the benefit vs the (assumed) increased processing time
 

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