Hey, y'all!  I just got done playing my first game in a West Marches-style campaign, and it had its ups and downs.  Here's a few questions to keep in mind as you read, and then the chronicle:

Questions

• How do you lie?  Several times the Thief wanted to baldface lie to someone and I wanted to do a CHA-based Defy Danger, which led me to...
• Subbing out Defy Danger key stat? Is that kosher?  Basically, it becomes an on-the-fly custom move?  The Thief, Valtar, was worried that might nerf some of his abilities later on.
• Everyone has to have rations?  What about the guy with 2 Load?  The Wizard is having a rough time of it.  Am I missing something about how overland exploration works, or is he going to have to ask the Paladin to ruck some stuff for him?  I'm fine either way, and I'm going to offer these guys a respec of their characters since they were my guinea pigs.  For any new characters, I'll have a better handle on what to warn them about.
• Moves for barter?  This is more a brainstorming note for myself, but with the party overland adventuring in an uncivilized land, they don't have a whole bunch of cashflow.  I've established that the local retired paladin will be taking reports on what they're doing.  Maybe he can give them gold in exchange for discovering geographic features or something?  Add something to the end of session move like When you tell Tanfael about your latest expedition... Or I just develop some sort of barter/tab system.
• Design Note: The Thief is also the hardest player I know when it comes to critiquing systems, especially of indie games.  He's pretty trad, but he has a real good feel for how and why he's trad--he understands game design.  He, after picking the Thief, looked over the Advanced Moves and said he wasn't terribly excited about advancement.  The new moves weren't much of a carrot to him.  Please take that as a single data point, and his personal opinion.
  

Lessons Learned

• Remember Armor-I totally blanked it for the squid.  Whoops!
• Look up rules about gang sizes, and make sure to implement them.  Partially justified because it was on the fly and I forgot, but the gang of crabs needed some bonus hitpoints and such.
• Five players might have been a little much to start with, because it was easy to let the action snowball away from some of them, and it was hard to keep track of all of their Bonds and such.
• Lead character creation better--Brandon the Ranger, who hadn't played much before, took some seriously suboptimal choices for an overland adventuring campaign, like a +0 CON and a Hawk that added a damage buff rather than foraging for rations.  One player recommended having a blurb in each character description about what stats might be important to that class.  I said "look at the moves you've chosen and the basic moves" but he was looking for more.  Maybe next time I'll have them choose moves before they assign stats.
• Uneven experience growth has to be dealt with somehow (by the GM, not the rules).  The bard's at 9 XP and everyone else is at 2 or 3 because I highlighted his CHA and he kept healing people.  Everyone else didn't get to make quite so many moves, or moves that were tailored to their highlighted stats.  That's on me.  Also, I kind of forgot to highlight stats until halfway through the fight with the squid.  Whoops!

There were five players

• Valtar Kim, going as Jack, a Human Thief
• Sanguinas, a Human Paladin
• Pendrell, an Elven Bard
• Fenfaril, an Elven Wizard
• Brandon, a Human Ranger

Play started on a ship headed for Landfall, a new settlement on the recently-popped-into-existence continent of New Aelfer.  After establishing bonds, which created a nice little web of intrigue, we opened with Pendrell playing music on the poop deck; Valtar and Sanguinas at the bow, observing the new land; Fenfaril below decks, packing up his travel lab; and Brandon in the crow's nest, getting the lay of the land.

The ship groans, and Valtar and Sanguinas discern realities.  Valtar hits, and asks what he should be on the lookout for.  I show him a flash of yellow and orange coming from beneath the ship, and a shipwreck a few hundred yards away.  Brandon scrambles down from the crow's nest.  As Valtar runs and screams about trouble, tentacles erupt from the water.  One snatches Sanguinas as he stares (on his missed discerning) at the ship wreck, and he's bound up tight.  The other grabs Brandon as he rushed to try and save Sanguinas and missed his hack and slash.  It's a giant squid (Level 2, 20 HP, Armor 2, snatching and ripping moves)!

There's a fight.  Pendrell plays healing arcane music and hits hard each time.  Valtar throws a knife (volley) and stabs the thing in the eye.  Sanguinas and Brandon fight the squid in the water, each dealing significant damage.  Sanguinas eventually lops off the end of the tentacle holding him, dealing enough damage to "kill" the squid, which sent it running back off to its lair to die in peace.  At one point, Fenfaril spouted lore, realizing that the creature wasn't just attacking to attack, it was attacking to show off, and that throwing some gold into the water might distract it.

After the fight, Pendrell tries does some more healing, but misses his second one, drawing attention (I filed this note away--a campaign front somewhere stirs!) and breaking a string on his mandolin.  Fenfaril tries to steal some of the gold he realized he could throw after the squid, but Valtar and Sanguinas catch him and there's some Parley and Sanguinas promises that the gold is meant to go to the adventurers anyway, as it's going into the Order's coffers to finance their expedition.

They get to land and meet the villagers.  Valtar is dismayed at the small size of the village, as there's no real chance for sneaky criminal activity.  He does, however, manage to steal the keys (tricks of the trade, with a soft hit: suspicion--steal jewlery and have Captain Harkas remember how handsy you were or cost: have to come back later to use the keys) to the lockbox.

Valtar and Pendrell set themselves up as celebrities in the small town of Landfall by telling tales of their exploits and Sanguinas talks with his superior in the town, Tanfael, about how everyone will be provided for (which leads to some questions on rations and such).

That night Valtar steals a longboat and sneaks back stealthy-like.  On a soft hit, he chooses "get in", so just as he's pulling himself up over the railing on the ship, he sees Bill, the night guard.  He convinces Bill (with no move) that he had actually been on the ship all night, and fallen over the railing when he was pissing because he was drunk.  He parleys with Bill in order to be left alone for the rest of the night, and Bill asks if Valtar will take his night watch post (the concrete promise, to allow Bill a night in the town).  Valtar agrees, runs off to scrape a few goldpieces of the lockbox (I rolled 2d12 to see how much he got, came up with 15), and plants some in Bill's bunk.

The next day at noon, the party meets and agrees to set off north around the coast.  Here's where things get a little messy--the beaches to the northwest of Landfall are one of the few places I didn't have much prepped.  As they go over the plains, they travel for two days in safe territory and start asking about tents.  I ruled that it was part of adventuring gear--which only two of them had.

Then they undertake a perilous journey, but they don't have that many rations and Brandon took a +0 Con (see lessons learned), so they keep it at one day and on a soft hit, they are followed.  I had Brandon roll alone for the whole group because the old rules left it open, and then when I realized that everyone had to do it themselves, the dice had been cast.  And we were running out of time.  And there were grumbles about me not preparing the players adequately for an overland adventure--not everyone could carry rations and a weapon, for instance.

What were they followed by, since I had no prep done?  Well, giant crabs, done up on the fly!  A group of 3, so 1+1 armor and 10 hitpoints.  They massacre the crabs.  Valtar sneaks around to get a backstab, and Brandon uses his hawk to buff both a Called Shot and a Volley.  Sanguinas hacked and slashed the other one and they dropped quick.  By this time we were at the end of our time, so they packed up, I didn't have them UPJ back home, just said "boom, end of session, you're home in Landfall, plus up your Bonds."

Thanks for the insight, Agony!  I haven't quite had a chance to digest it all, but it looks like a lot of good experience.  Your threads here and on Obsidian Portal have helped me figure out what I can expect and how I want to set this up.

Here's one thing that I have thought about--I'm going to be sticking pretty close to the original West Marches's conceit that the PCs are the baddest asses around.  Carouse has two options that make me a little uncomfortable.  Befriending a useful NPC would lead to rehashed ground pretty quickly, I think, in a town of about 100 people, and nobody around Landfall is going to be ensorcelling them, and I can only do so many "the farmer's daughter thinks your cute" results.  In such a small town, people tricking our entangling is going to get real messy real quick.

So I've written a custom move to replace it.  This is actually the first custom move I've ever written, so let me know what you think:

When you throw a party at the Sainted Yarlow to celebrate your victory...
Mark XP and Roll+Con.  10+ 3, 7-9 1.

• Someone tells a story you're unfamiliar with--the GM will tell you how it affects your map.
• Your tales attract a follower--take a hireling of your choice and consider his first Cost paid
• You don't make a brash promise or bet.
• You had a good night of gambling.  Win Lvl+Cha gold.

I like Carouse as written just fine for larger communities or those with more badasses around, like your Ravencamp, Agony.  If something like that ends up getting founded, I'll definitely include it.  It just doesn't feel right for this little farming town.

So here are my WM-specific questions I'll be hacking on. No formatting this time, since I'm on my phone.

-Does Carouse fit as written in a WM setup, with quiet NPCs? How can it be hacked, becaus it's awesome, but they are living in a reaaaly small town.
-See above for Outstanding Warrants, Familiarity, Veteran... Have these moves just been nerfed, or is there a way to keep their awesome?
-Same thing, ish, for Bardic Lore (are there songs about this land?) and Well Travelled.
-How will UPJ work when theyre seeking the unknown and exploration is a part of the fun. Should I make a "when you wander a hex..." move? Or reinstitute Adventure Hook?

I think that's about it. I'm in the very basic steps of world creation at this point.

Here's a question specifically for you, Agony. How much of the shared/improv worldbuilding have you kept? Have you gone West Marches route of knowing the history and statting honestly? Or has it been more improv style?  Do you use random encounter tables?  I really like some of the work Zak S. over at DnD with Porn Stars has been doing, and I'd like to incorporate it if possible.