I've been working on this plenty more, and on Friday night I ran my first playtest, which went really well overall. I think there's room for improvement, but it's the kind of thing where DW's shortcomings are subtle enough that it's hard to know what needs to be done.
The good news was that the setup worked really well, and made it easy to come up with a starting situation. The PCs were a Pure Sacrifice (a princess burdened by Destiny), a Dumb Fighter, and a Conniving Thief. Each character has two Temptations, and then a Heart's Desire (which is a more specific thing stemming from one of the temptations). Combined with Hx, we got a situation where the Pure Sacrifice had to journey to another city to retrieve the All-Seeing Eye of Agamato, with the fighter her sworn protector and the thief both obsessed with stealing the Eye and secretly in love with the Sacrifice. Much wackiness ensued with the dread necromancer's undead minions attacking.
The game presently has 5 stats:
Charm (manipulate someone)
Guts (endure strife, kick some ass)
Magic (spout lore)
Sanity (act sensibly despite temptation)
Wits (read someone, run away)
I think having both endure strife and kick some ass on the same stat may have been a mistake, since the Dumb Fighter's Guts+2 let her handle *every* combat situation really well. (Though it didn't help that neither of the other PCs took moves that would let them do well in combat.) But then I'm really not sure how to rearrange the stats.
I think I'm still getting the hang of writing up character types, because relatively few non-basic moves came into play during the game. (Also, I gave the Pure Sacrifice some moves that key off of her being captured, which seems to be too specific without some mechanism to have her be captured a lot.) I'm also concerned that I've given character types too many moves that go off of their best attribute, but I'm not sure how much that's a thing to really worry about in AW.
But, working on new character types is still really, really fun, and I've found that people who take an interest in the game very frequently have suggestions for new character types. I have a list of like 20 possible ones, and I'm currently writing up the Angsty Shadow Warrior (for Drizzt and other angsty born in darkness types), the Chosen Visitor (a Japanese teenager who's been pulled into the fantasy world), and Psycho Warlord (a take on the D&D4e warlord class, though I may need to come up with a better name).
Another nifty thing I added was a "scenes from a hat" rule, which you can use in place of the random event table, either preemptively or after the table gets stale, which is where the MC asks the players a leading question ("What's weird thing could happen while you're fighting undead?"), which they write on slips of paper to be drawn randomly. That's how the game ended up having its own version of Murray the Demonic Skull from Monkey Island.
My friends were pretty happy with the result and want to play more, so while it needs more work, I think it's on the right track at least.