Second issue is maybe more specific to AW, since it pertains to defining exactly what the different moves cover. Because of the stealth stuff on pages 192 and 270, there's not much room for adding stealth to AW through character moves.
Let's say I add a stealthy character move like this one:
Stealthy: when you move, silent, unseen, roll+cool. On a 10+, choose 2. On a 7-9, choose 1:
-- you infiltrate a secure location
-- you get close to someone or something
-- you go undetected
On a miss, none of these and you've been caught out, vulnerable, by hostile foes.
This may or may not be much of an awesome special move. It might simply be a case where you spend one of your choices on something that the MC lets everybody do. Which is very similar to the phenomena where you spend a choice on something and then the GM takes it away.
John Harper wrote a post about when one of his players assembled a gang in the fiction, as opposed to by taking an improvement, and John let him use the Pack Alpha move when he bossed them around, pretty much like an MC custom move. Now, I'm against that, partly because, unlike the rules for angel kits and workspaces, Pack Alpha is explicitly a Chopper move. Every character starts with 3 special things, and if somebody gets one for free, it removes meaning from the choice to take it instead of something else in the first place—although it's not as bad as the Savvyhead who starts the game watching his workshop get blown up, since you're not taking away anything somebody has in game. I'm not against the character getting a gang—that's fictional, not mechanical. He went out and assembled a gang, rock on, but my interpretation of Pack Alpha is that it comes with the Chopper, not with the gang.
Here's a better example: What if I take Eye on the Door so I can roll+cool to escape, and then the MC basically uses that move for acting under fire when anybody wants to escape? (The wording's pretty similar). Well, then I just wasted one of my choices. I could have taken something else instead and had some other way to be awesome and get some spotlight time and differentiate my character. I'm not losing my stuff, and yet I kinda am.
If the MC consistently lets anybody roll+cool to escape from anything, the move means nothing. If the MC sometimes says "no, you can't get out of this one," then you can point to your move, name your escape route, and roll, and the MC can't say no. If escaping is far more granular than just one roll usually, then taking the move is just as awesome as something like Lost or Things Speak. But it all depends on the MC, because that line isn't particularly well-defined in the game—although the existence of character moves allowing escape should be enough to avoid the situation where taking the move means nothing.
Acting under fire doesn't actually say anything about escaping, but it does cover stealth, so that Stealthy move above is more likely to become useless than Eye of the Door is. One solution, if you're sticking with the basic AW rules, might be to change tactics, and make a stealth move that does something different than the basic moves do, like this maybe:
Stealthy: when you take steps to conceal your activities, roll+cool. On a 10+, hold 3. On a 7-9, hold 2. Spend your hold 1-for-1 to take action and remain undetected, as much as is possible. If you reveal yourself, lose any remaining hold. On a miss, somebody's on to you.
If you're re-writing the game (as in Bulwark), you can do other things. You can keep it like AW. You can make Stealthy a separate stat with new basic moves. You can require a special move for characters to be stealthy—no move, no sneaking past people. Or you can set up two different levels, so you can sort-of sneak around without the move, and sneak around really well if you do have the move.
With the stat set-up we've been discussing, you can just roll your stat dice to sneak around, but if you have evade+2, then there's the bonus, so you do it better.
Another option would be to have a generic shitty move, with a special move where the results are better, without using different numbers. For example, if you don't have one of the special Stealthy moves above, you have to use this one:
When you do something dangerous, roll+cool. On a hit, you do it, but on a 10+, choose 1, on a 7-9, choose 2:
-- you get hosed for it now
-- you get hosed for it later
-- somebody close to you gets hosed instead
So, some stuff to think about.