Hi Michael! Thanks for playing. That was a fun session.
1. It is possible, I think, now that you've played it, but I don't think anyone has done that yet. So... good luck! :)
2. You can't pile them on, no. You blow off some steam, you roll, and you're done. You can't make the move again until you blow off some steam again... presumably after you accumulate some steam. In the AW text, this idea is called "to do it, do it," which you'll see in the PDF. It just means, "to roll a move, you have to satisfy the fictional trigger."
3. No. :)
4. I haven't tweaked the OP based on their plan, but that's an interesting idea. I could see giving a +/-1 there, maybe, depending on the situation.
5. You'll have to wait for the Kickstarter.
6. Yep.
7. Yeah. I ran out of room and cut the obvious ones.
8. That's right.
9. The Regiment and AW work the same way when it comes to GM moves, but I find that there are pernicious myths about how GM moves work in AW, so it's hard to know how to answer.
In both games, the GM can 'inflict harm as established' as a move, and you don't have to wait for a miss to make a move. It's a bit less fraught in TR, since harm is randomized.