Bookkeeping disappeared. Creating encounters and villains couldn’t be easier. Since I don’t spend my time on those things I can keep the story going and have plenty of time to be creative.

In other words, we live squarely in Troy’s #5. Totally. My PC’s use ‘Basic Social’, ‘Basic Etiquitte’, and such as much as Hit Points.
Transition Sessions are often a few sessions long, by the examples given above.

I give a flat xp award at the end of each session. Good play and other bonus stuff I reward with extra fate points.

Shopping is between missions, either in on your Yahoo group site or in the first 10 minutes of the next mission. If you want more time than that learn to use our Yahoo Group site.

I never do cleanup . “In the rest of the area you get a bunch of junk that covers your expenses of your pirate crew / henchmen / taxes / bribes / donations to the church / drinks / …” Plus clues to the next adventure. If they past some big toy they’ll need in the next adventure, they can find it on the way there.

I do use traveling time transition encounters and events to highlight some cool bit of the world or shine the spotlight on a player character. And as I said before, if they need the Flashlight of Wazzo in the next adventure and missed it in the previous one, they find it one the way there, often being used to blinding effect by some opponent.

My inclination would be to make the XP reward match the approach. Maybe 1/x (with x being the total number of party members) of what they would receive normally?

GM: “Okay guys, you’ve killed the Grand Pooh-Bah, what’s the plan for clearing the rest of this dungeon?”

Party: “We take it room by room, announcing our presence and what we’ve done, checking for traps at all the obvious places, and fighting everything that resists.”

GM: “Cool. Everyone make your best attack roll, and whoever will do the announcing, make me a Bluff or Intimidate roll. And whoever has the best Perception, make me a check. Results?”

Party: “One crit, one fumble, and these numbers… The bluff was moderate, but we are carrying the Pooh-Bah’s head on a pike; that should count for something. Natural 19 on the spot check.”

GM: “Gruesome, but effective. As you make your way through the dungeon, some of the critters flee, some fight, and some want to talk about it. Ms. Crit gets away with no damage, and even manages to find this map. Mr. Fumble manages to bend his sword and lose 80% of his hit points. And Eagle Eyes here finds a secret door.” (Hands out damage or treasure, depending on die rolls, and roleplays out the encounter behind the secret door.)

Scott: Great list! Those all make sense in a D&D context.

As I said above, my head is currently in Burning Wheel and all of those are rife for full-on play. For example, one of my players’ characters was looking for a rumour of organized crime in a large town he was new to. He wound up with someone he thought was the main player, but who had discovered someone nosing about and sent goons to bring him in. He had a duel of wits to save his skin and wound up convincing the high-ranking enforcer to host him and make use of his skills, earning him an enemy in the form of the goon who wanted him tied to a rock and tossed into the river.

Planning for four hours and executing the plan for an hour is a lot less satisfying than planning for 30 minutes and executing the plan for an hour and a half. The extra 30 minutes being for the screaming adjustments on the fly part of it.

For freeform/sandbox games, any of the above might be a good way to pick your next adventure. Often, though, the GM has one or two ways to get you into the next adventure… and you may stumble around roleplaying lots of conversations until you finally hit on the right one. If the party splits up, so you have to wait a half hour for your five minute time-slice, and it turns out to be a bad guess [hmm... no useful rumors in the tavern after all], it can take quite a while.

Combine that with everyone competing to do stuff focused on their PC [interacting with their NPC friends, disposing of personal loot and ordering new supplies, finding leads to the person who has the item they want to buy, etc.], and a lot of time can pass.

Clear sign posting can avoid some of this, but not everything. Similarly, if you “clean out the dungeon” after you’ve fought the head villain, few of the encounters will be challenging or exciting– but if you break out the battlemat, it can take hours to go through the combats. If the GM has hinted that you’d better be the next level before going on the next adventure, and XP comes from combat… you get the cleaning crew.

In terms of planning, I’ve always found that to be quite fun. I remember a cyberpunk game where we all planned for 5 hours how to orchestrate a break-in, with the actual play of that taking only 1.5 hours. We had a blast planning. Like Troy said, it depends on the players’ preferences and what, exactly, the planning is for. Sometimes it’s unrelenting table chatter/debate, but sometimes it’s in-character planning (or at least quite interesting table chatter).

The one thing I’m still a bit confused about is how a transition session would take an actual session in terms of seeing it through. Do they not take significantly less time, usually? Again, I’ve never (or very rarely) had a transition type of situation in D&D and, with Burning Wheel, never.

When the downtime between dungeons or “plot points” (the trip into town) stagnates into a long Wal*Mart visit, Salvation Army drop, and conversation at the tavern, it becomes more of a transition session than an adventure session.

Not that these things can’t be done or even played out in roleplay mode, but when an entire evening is taken up by mundane minutia, it can be quite boring and tedious for a lot of folks wanting to get back to the excitement.

Am I missing a key part of what makes this kind of situation in-game different from any other?

Depending on the in game situation, this type of session can be minimized– but doing so can throw off the game’s expectations. If you don’t let people convert “junk” to useful items, they’ll probably be fighting below expectation until they have a chance to right the situation.

Your comment about resistance to taking between session events to email is also right on. I have a two players who would happily deal with selling, etc., between sessions. But at least three other players don’t read/respond during the week, so you can’t actually skip the session…

I recently read about a technique called “say yes or face the dungeon” that might be of interest to people who are having a tough time with this kind of play.