The Obvious Answer

The pat answer is that the player is clearly signalling that they aren't interested in simulating time spent in town with any degree of granularity. They want to show up, hit sell, and get on with the adventure.

The sense of time compression may be a result of their minimizing the importance of the tasks. It could be because they feel "penalized" when they're told that a task takes too long. Or it could be that they're concerned that they'll be caught in mid-task if it takes too long.

In any event, it seems clear that the player isn't that interested in sitting around in town for too long. Is this something that you can compromise on?

A More Useful Answer

All right, so we all hate the obvious answer.

In my games I've always worked the abstraction. I go around the table, and each player tells me everything they want to do at a high level (i.e. "sell my stuff, and look for magic armor +8"). I tell them how long it will take (and what rolls are necessary), and give them an opportunity to modify their request. Then move on to the next person.

Once you get an idea of what everyone's doing, sprinkle in role playing scenes and random encounters in montage fashion. Just avoid springing anything that's likely to interrupt the overall process.

This is essentially the same concept as crafting. You wouldn't let a player give you the blow-by-blow of their crafting session to save a little time. The same applies here.

Increasing abstraction does, necessarily, decrease the opportunity for role playing. It doesn't eliminate it in this case, but it is something to be aware of.

Introductions

The real problem you're going to have is changing how you've been doing things. Players are going to have a hard time going from doing something in a day to doing something in a week, even if there's no mechanical difference.

Step one is to communicate with the players.

After that, give them useful choices when it comes time to make their rolls. If they want to sell something faster, give them a range of options (you get full book value if you wait several months; half if you sell in a nominal timeframe; quarter if it must go now).

If a roll is required, give them the option of increasing the difficulty to accomplish the task in less time (i.e. base time one week, subtract one day for every five added to the difficulty). Failure means a reroll, resulting in things taking longer.

And bribery never hurts... If nothing else, giving them something they couldn't otherwise get through taking extra time (a bit higher sell value, a cheaper price, and so on) can help swing things in your favor.

Some More Thoughts

Sleeping on this, it occurred to me that human beings actually act like this all the time. We strive very hard not to be idle during our daily lives.

The big difference is that we favor low-activity tasks that give us biological incentives: We savor our meals, engage in idle conversation, read books, watch TV, sleep late, etc.

The gap you're seeing between "realistic" behavior and what the PCs are doing is because they've stripped out all of this idle activity. Why? Because they're not receiving the real-world incentive for this sort of thing (dopamine, endorphins, etc.) and these activities are extremely boring to roleplay.

The Urban Campaign

One of the key assumptions of most of the above is that in town means downtime. Encounters continue, but the assumption is that these encounters will usually be more socially oriented, less threatening overall, and unlikely to disrupt the ongoing processes of town life.

This lets players fudge their sheets a bit. It doesn't matter whether you have that new sword yet or not, you can still take part in what's going on without holding anyone back.

Campaigns with a heavy urban component violate all of these assumptions. Players need to be in top form at all times, because a top-tier encounter could happen, or a thread could pull them out of town on short notice.

In this case, waiting a week for an item to be found gives the players an awkward choice:

• Be actively looking for the item for a full week. Sit idle while the rest of the group enjoys a week's worth of adventuring.

• Endure pointless red tape. You've picked the item you want, you've probably paid the money, you've made the roll, but you can't update your sheet until the GM nods at you some arbitrary point in time later.

• Get the item right away, but "say" you're taking a week to get it. Wha..?

In any case, that's a lot of annoyance for a pretty small gain in verisimilitude (or a really weird drop in verisimilitude for no perceived value).

Urban Solutions

While it's harder to do, there are still a few things you can try to mitigate these tendencies.

Employ Gating

Give the players a buy limit. They're free to buy whatever they want, as long as its value is below X. This will tend to lead to periodic frenzies of buying, making it easier for you to lock down the game world, and decrease the problems listed above.

Whenever you increase the buying threshold, treat that as downtime, and abstract it as described above. Minimize active top-tier adventuring, and let the players go nuts.

The goal is to get everyone buying at the same time (so hopefully the players aren't poking the game world), and to have the game world stop poking them back long enough for them to get their items.

Skinned Gating

I'm still having trouble groking your full situation and requirements, but for the sake of posterity here's some notes on skinning a gating system. I don't think this will necessarily work for you; it requires periodic lulls where the game-world isn't actively trying to get the PCs attention. You can come up with individual reasons, but there's no really good general-purpose reason for this (although it's worth noting: If your game world is constantly poking at the PCs, that may be part of the issue).

Step One: Establish the gates

The first step is to divide the items in the game into different gates. Most DMs use gold-piece value (i.e. a buy limit) because a. all buyable items have one, and b. it's roughly equivalent to how powerful the item is.

That said, you have other options. Some systems support legality and availability codes for individual items (Shadowrun and D6 Star Wars come to mind). You can, naturally, come up with ratings of your own.

Step Two: Apply the gates to your players

Most DMs simply leave the gating itself up to the players. "You can buy anything up X gold-pieces;" "You can buy anything up to availability 3." This has the advantage of decreasing the amount of player/DM bandwidth (a very limited commodity), but can feel kind of gamey.

You can soften this up a bit by keeping availability somewhat secret ("That's a highly regulated item"), and having the players ask for it.

You can also use "soft" gates to make things feel a bit more organic. An at-gate item might be a nominal difficulty, a significantly below-gate item an easy check, and an above-gate item extremely hard.

The down side to these techniques, of course, is that they occupy table time. The upside is that they make things feel a bit more organic and mysterious.

Step Three: Advancing Gates

There are several different techniques you can use to explain a gate advancement. Here are a few examples. I'll tend to use numbers in the explanation, but you can of course use in-world explanations.

• Location, location, location.

  In our little town, you can only get availability 3 items. Make the trip to the capital and you can get up to availability 6. Find a safe route to the lost city of the dwarves, and you can get availability 12 items!

  This is particularly effective if the goal is to move the players around over the course of the campaign.

• New blood in town

  As the story progresses, the players' influence may result in the city becoming more favorable to merchants (either legitimate or not-so-much). Or perhaps the city is simply growing over time (depending on your setting). Either way, an influx of new merchants or the establishment of new trade routes could be used to explain a higher gate-level.

• Powerful allies

  NPC wizards, craftsmen, nobles, or merchants helped or extorted by the PCs could all be used as an explanation for a higher gate level. Either through crafting the items directly, allowing access to vaults, or by using their connections to import the desired items.

• Licenses

  If you use legality as a factor in item availability, you can turn the acquisition of licenses or special dispensations into quest hooks of their own.

Change your magic paradigm

In your description above, it sounds like you're leaning towards the "magic items are special and unique" school of play, while your players are leaning towards the "magic items are an integral part of the character" school of play.

You could always try yanking the dial all the way over to the "magic items are special and unique" school, and eliminate the ambiguity. Players don't shop for magic items... They encounter them in quests and adventures.

If you go this route, be sure to give the optimizers something to replace the magic items they used to find easily (so they don't feel less powerful as a result). Something along the lines of the "inate bonuses" concept in D&Doid games.

As usual, communicate, let the players know that things are changing, etc.

I hope they pass, and try to plot for them passing but I feel like I need a swoop-and-save always in the wings.

Ah, here we clearly have part of the problem. They're in a situation where they would fail most of the time if you weren't engineering things for them to succeed, so they should fail some or most of the time. If you feel bad for railroading them or for removing the challenge from the game by ensuring that they don't fail, stop doing that.

PCs don't need to succeed all the time, especially when the danger isn't lethal. Failure can be instructive and even fun! (Even, dare I say it, . . . "character building"?) Honor is so important in that setting that a moment of lost honor, a recognition that they aren't perfect in all things, can do wonders in terms of future character motivation. Plan for the characters to fail.

That is not to say that they should never succeed or not learn anything, though, but there are ways of doing that without having direct social-roll confrontations or even after failing at all direct confrontations.

First, don't worry about giving them a loyal subordinate with the social skills to take on the courtiers some of the time, and don't worry about fudging the rolls for him up or down if you have to . . . maybe he's talented but new and prone to rookie mistakes or getting rather old and not as fast or perceptive as he used to be. Also, don't worry about having him advise the PCs. However, his advice shouldn't just be "do this"; have him offer multiple options with pros and cons and let things play out from there. Heck, let him be wrong sometimes just so the PCs don't rely on him too heavily. (A sufficiently deep intrigue will have elements he couldn't expect, or that were expecting him. . . .)

Second, give them plots where their bumbling or social weaknesses are strengths. Have enemies overestimate them and plan for the wrong reaction from the PCs, have their bumbling somehow convince everyone that they know more than they do (spooking the enemy into making mistakes), have them accidentally round up all the right people for all the wrong reasons and someone confesses to the plot and then asks how they knew, or just plain have things come to a point where the villains are expecting some nuanced social reaction they can parry and the heroes decide to just charge in and take care of things the old-fashioned way.

There's one more option: The overestimated idiot at the center of a backstabbing circle. In social politics, this is where everyone tries to curry favor with the lord by telling on everyone else. As a result, the lord is spectacularly well-informed about everyone else's secrets and develops a reputation for being an omnicient badass when all they had to do was sit there and look stern and knowing. If your players can handle that kind of information effectively, they'll find ways of taking care of business without ever having to make a social roll they don't like.