Sadly, I just have a suspicion: at first, DW seemed weird and different when it comes to those rolls, but then having the same odds no matter how good or experienced a character is does seem to be very similar to how D&D 3.5 worked for me over many campaigns. As our skills went up, so did the DCs. As our to-hit values went up, so did our ACs. In classic D&D, there are no skill checks but attribute checks remain the same no matter what. Not much different! And since characters not specializing in their skills had basically no chance to make their rolls, that feels a lot like a self assembled list of moves. (Leaving the back and forth of player moves and GM moves aside for now.)
In classic D&D, the situation is different in combat because the two sides don’t keep on climbing. ACs go down, but not forever (maybe if you use Gary Gygax’s Monster Manuals with their devils and demons). Effectively, there are situations we can simply ignore. Meeting 1–6 orcs is not an encounter after you reach a certain level. DW would simply say that the move says you announce future badness and a handful of orcs just ain’t that. All in all, I feel these DW aspects are not too different from D&D as it is played at my table.