Halflings are optimists. They are friendly, lucky and have no fear. Grumpy and pessimistic halfling would be the subversion. But I agree that halflings in D&D are not as clearly defined as they could be, (and this is the third time I say this) it is because they can't decide whether they're kender or hobbits.Halflings don't really have that. They're short people that are lucky, for some reason, and brave, for another unexplained reason (even though their race is the embodiment of "hide from our enemies, and we'll be okay". If they don't have much core identity in the base of the game other than "short people with a smattering of traits to make them worth taking and mechanically different from humans", that makes it even harder to subvert the race's tropes.