This makes the play sound more like gaming the DM. You have to be able to anticipate how the dm will react to get any progress. which I think is definitely a type of skill in skilled play in many situations. Im just not sure how that relates to achieving or failing your goals in DW.
I mean is it unskilled play if the dm doesn’t determine your particular actions warrant a beneficial move to you? Are you going to fail to achieve your goal if that happens?
Well, I think this is where you kind of have to do the paradigm shift. The GM is not out to thwart the players. I mean, that isn't REALLY true in GSP either, but its much less true here in a sense. So, the GM is going to think "I WANT the dwarf to do this clever thing and get this hold, because that will be an excellent 'horn' for my next dilemma!" That is it can certainly sharpen one of the horns, like "ouch! Do I take advantage of my hold, or do I uphold my bond to the halfling?" Guess what? The GM's job DEFINITELY is to make that problem appear for the dwarf! The skilled play will help them all. It can be kind of a tough job to get DW to 'burn' if all the players are really not going to engage with this problems too. But usually you can start with classic D&D tropes and bootstrap from there:
So, maybe you have some players who want to play B/X style crawl narrative basically. They might create characters with stated goals like 'get rich', 'find out what happened to my father in the dungeon', or 'find the holy sword of Gorgonzola!' (this guy is The Paladin, he's trouble, lol). Their alignments and bonds are probably all over the place, but they still work. Through some questions you all cook up a B1-esque scenario, there's a dungeon maze, they want to delve in it. OK, well, the GM isn't going to make up a map with all the rooms and corridors. He's going to make up some areas, maybe some ideas for interesting encounters, and maybe build an adventure front to be an initial obstacle.
The PCs are going to head into this thing, and the GM will say something about coming to a T intersection, describe left and right, and ask the great question, which way do you go? Now maybe the halfling thief creeps ahead to the right, the dwarf notices he's about to step on some unstable stonework, and he manages to fulfill his bond to the halfling (by saving his arse)! We're off to the races. It will take a while to build this into something thrilling, but pretty soon their going to start finding maps, clues, a brewing threat to the town, etc. and they SHOULD learn to use their moves and get clever, right? Maybe not. Maybe they're the sort of players that just reflect everything back on the GM and remain noncommital at all times... Meh, those guys might be better off in the real B1...