There's a lot of stuff in there.  Too much to answer right now but I'm sure others will chime in.  For now I just want to give you two links that you might find useful.

Star World *W hack by Rob Wieland and Mark Diaz Truman - includes ship officer classes, special basic moves and ship moves.

Pirate Class for DW by Melissa Fisher - it's the nautical kind of pirate, but it should give you some ideas for piratey moves and color.

Good point T.G. made about encouraging proactivity.  I have a similar group and I do need to remind them: "To make things happen, DO THINGS." :-)  At first only one of them really "got it" - and she leveled up twice as fast as everyone else!  Now the rest are beginning to get the picture (I think).

@dudemic - I want to talk about the difference between a plot and a countdown.  Basically... there's a step between "seeing a conflict ahead of time" and "guiding the players toward it".  Don't take that step.  The Countdown Clock (or Portents, since I prefer to use the Dungeon World approach here) is all you need.  It has its own innate sense of progression or escalation, but no dictation of player actions.  Just let your threats and moves be experienced by the PCs, and if they choose to go in that direction, then go with them.  If not, use a move (when you feel like it) to progress the Front to its next segment/portent.  An example might help.  Here are two Fronts from my current AW campaign:

FRONT: Megadeth - Brute/Chopper (Leader of the Reapers) IMPULSE: •   To control the east side STAKES: •   Will he ever figure out who is killing his men? •   Will his Alpha status be challenged? •   Will OG King move in on his territory? PORTENTS: •   Sound of motorcycle engines nearby, unseen •   Tales of people being interrogated by Reapers •   Being followed/observed by a pack of riders •   Someplace gets shot up by the MG on a jeep •   Battle between King’s men and Reapers

FRONT: O.G. King - Hardholder of "GG" (Golden Gardens) expanding his turf IMPULSE: •   To control all trade in Vegas STAKES: •   Will GG take over the Strip? •   Will GG suppress the Reapers? •   Will King get taken out by the assassin from LA? PORTENTS: •   More GG patrols on streets •   GG tagging appearing on new blocks •   Firefights between GG and local scav crews •   Firefights between GG and Reaper squads

As you can see, Megadeth and King seem poised for a conflict.  Anyone in town could tell you that, they might even try to give you odds on it.  The portents show me what's going to happen IF THINGS PROGRESS WITHOUT CHANGE.  Eventually either Megadeth or King will get to that point where they begin an open war with the other one.  But.... then again, it's totally possible (in fact it's highly likely) that the PCs will inject themselves into the mix before that, which means I have ZERO IDEA what will happen.  Which is exactly as it should be.

Backing up now.  Let's say for whatever reason, the players keep witnessing all these portents but decide to do nothing to insert themselves into the action.  So...  The Reapers are constantly tailing and shaking down both the PCs and their NPC friends, places are getting shot up, Golden Garden tags are appearing on block after block, some local scavengers (whom the PCs probably know) are getting shot and beaten... and the PCs are still doing nothing?  Okay then, if something else hasn't happened to change the whole situation (say King avoids getting killed by that assassin who happens to be after him), then a wholesale war would erupt between the two gangs.  It's possible.  It's probable, if nothing else happens.  But that's not likely.  Dig?

"Knowing what's possible" and "pushing toward it" are two very different things.  The most important difference is this: When you are plotting, you are planning for what the PCs will do.  But when writing portents, you plan as if the PCs weren't there.  The portents show what will happen if the PCs do NOTHING.  But we all know they're not gonna do nothing.  And that means your plans (or rather, your NPCs plans) are gonna get FUCKED UP, my friend.

Which is exactly as it should be. :-)

Best way to decide on a Threat type is to look at their moves.

In my current campaign I have a Grotesque who is also a mindfucker (she visits people through the maelstrom and messes with their perception of things, tries to seduce them, tells lies about people they know, etc).  She is also the ruler of a group of infected parasite victims whom she controls telepathically.  Her followers are called "Cordies".  I could have made the Cordies a separate threat, but since she's a secretive person and they are tightly under her control, I decided to treat them as a direct extension of her.  So when I/she makes a Grotesque move like "Put her in someone's path", I put some Cordies in the path instead.  But if you follow these luckless victims, eventually they will lead you to her.

Just wanted to say thanks for picking this up.  I loved the original concept and I didn't want it to fall out of existence.

I suggest to start with the Principles and MC Moves.

I'm reposting this here because I'm interested to hear Vincent's reading.

Personally, I take the word "Obligation" to mean an onus to deliver something to another person. You're right that a couple of the obligation gigs seem more personal than interpersonal, but I read those socially, because the word used is "Obligation", not "Elective" or something else.  In other words, I would take "Pursuing Luxury" to be an obligation to live up to some luxurious standard set by your family, clan, mentor, boss or whatever, for social purposes. I would take "Maintaining Honor" to be an obligation to your unit, commander, flag, rank, mentor, sensei or whatever, for purposes of maintaining social status & face.

The question isn't whether these can be ignored; all gigs can be ignored if you choose not to work them. The question is "what makes them obligatory?" I believe the answer in the case of the "social" ones would be something like "because to do otherwise would be to bring shame, dishonor, downfall, ostracism, judgment, etc to (someone)."

I'm not 100% sure of the above. I'm not even sure if it's an important distinction to make (personal vs interpersonal), as long as it is felt as an OBLIGATION.  I suppose a neurosis would count, as long as it truly compels character behavior.

But in Lafferty's case, it feels like it doesn't.

Complications have now been added to the NPC Generator.  To generate them along with your NPCs, hit the URL this way:
http://asifproductions.com/aw_npc_gen.php?complication=1