This is less focused than I like to normally post, but here it is.
THE MAPSession one, I show the PCs a piece of paper with a dot in one corner. This is a city. Closer to the city there are towns and villages and further out there are just villages. Even further out it's basically just outposts, a few villages along the border and the like. I don't know how many, we've not been there yet.
So, let's pick a town and a village, where are they?
Let's make some character thumbnails, three each (including the me, the GM), and they'll be from either the village or the town. Now, everyone creates a single character based on one of those thumbnails, etc, etc.
You'll likely start play in whichever of the two locations is further out from civilization.
In the next session, I'll have hexmap of the immediate environs sorted out (thanks, Welsh Piper!), but we don't need to worry about that yet.
THINGS ABOUT SETTLEMENTSWhen I say "settlement" I mean, "a place with some kind of at least semi-permanent structure and people living in it," which can mean a whole slew of things.
Assuming the GM knows about as much about a settlement as the players, there are some immediate questions about what the place looks like.
You could rely on the Pathfinder SRD for Settlement size or you could just pull stuff largely out of your ass, which is what I like to do, because I'm much less concerned with how many people there are in a given settlement than how many people it "feels like" are there. There are camps, outposts, villages, towns, forts and cities.
Camps have about 20 or fewer people and are hunter-gatherers/subsistence farmers, maybe a religious/political commune, maybe refugees, maybe a village in serious decline, maybe a hunting lodge or the like. (Reaction to adventurers: Neutral or Chaotic Needy)
Outposts have as few people as camps but maybe more (as many as a town in rare circumstance) and are dedicated to very specific tasks and are usually built in an ad hoc manner. The more common are military outposts, outposts for scientific or magical research and outposts dedicate to some kind of labor like quarrying, foresting, mining, etc. Research or labor outposts are often quite noisy. (Reaction to adventurers: Neutral Indifferent)
Villages have enough people to form some moderate degree of hierarchy and there is usually a religious leader, political leader, maybe a couple of trade specialists, while most people aren't living terribly far above subsistence farming. (Reaction to adventurers: Neutral Wary)
Forts include castles held by nobility, large military installations, and fortified wizardly or clerical enclaves. They likely have fewer people than a village and are highly idiosyncratic. Usually have a single reliable point of access to trade. (Reaction to adventurers: Neutral Wary or Indifferent, unless the head honcho of the fort is a total dick, in which case, AVOID)
Towns have plenty of hierarchy likely multiple religions, and some bureaucracy, possibly taxes/levees, etc. There are likely lower, middle and upper classes here. To survive as such, a town has to be associated with some nearby farming villages and communities and are often intermediaries between food sources and cities; accordingly, Towns are always central to the maintenance of trade routes. Most towns have walls, somewhere, though they may have long grown beyond their walls. (Reaction to adventurers: Neutral Disgusted)
Cities are large, with a much greater distance between the upper classes and the rest of the citizenry. The bureaucracy is bloated and byzantine, taxes are often oppressive and arbitrary, and there are usually a whole lot of really poor people. Cities may or may not be walled and any such defensive structures are probably out of date and in disrepair. Cities are generally well-positioned near large, reliable food sources - usually there are a lot of farms nearby and/or they're on the water. (Reaction to adventurers: Neutral Unreliable or Dangerous)
WHAT'S THAT SMELL?
Camps, outposts, villages and forts are all likely built largely out of ambient material (if near a forest, wood; grasslands, likely poor quality brick; near stones, likely piled rock). Forts and outposts may have central structures built with more modern, refined materials, but these are likely in disrepair and decay if the settlement has been around for long.
Villagers, and possibly some townsfolk that deal in livestock, likely share their sleeping quarters with their animals.
Towns might have cobbled streets and Cities almost always do, but anything smaller is usually just dirt roads and mud (and of course, excrement and rotting food). Towns might have a sewer and Cities almost always do, but, of course because dungeons and monsters are metastatic and virulent, the sewer is likely a haven of Old One trans-dimensional spider monsters or chaos cultists or punk priests or vampire gangs. Similarly, as trade routes are cut off by war, dungeon or monster incursion or other natural disasters, towns, villages and even cities contract and die off, ceding the remaining edifice to dungeons and monsters.
Really new settlements may stink of the building materials (sap, sawdust, mud, dust). And most have that delightful beast of burden smell. Likely everything larger than a village smells a bit like a latrine (including Forts). In towns and cities, the poor likely like in the oldest, crummiest buildings, likely closest to areas of employment and lowest to sea level.
WHERE YOU SLEEP
It's always safe to assume that there is a place to stay. If you've got enough valuable stuff (more on that in a second), the locals might even offer you their beds while they go bunk outside or with the neighbors. It's not always safe to assume that they've got stuff you need or can afford to give you money for what you want to sell.
The B/X equipment list has like twenty things on it. Here is my take on it:
1. Portable containers (Backpacks, large sacks, small sacks, drinking skins)
2. Food (Standard Rations, Meals)
3. Small Hammer
4. Wooden Pole (10')
5. Wine/water/beer (quart)
6. Torches (6)
7. Tinder Box
8. Rope (50' length)
9. Flask of Oil
10. Iron Rations
13. Thieves' Tools
14. Holy Symbol
15. Vial of Holy Water
16. Specialty items (herbs, medicinal potions, or anything else not included in the above)
CAMPS AND OUTPOSTS
Camps and Outposts at any given time have d6 of items 1-6 for sale and they likely can't buy much of anything off of you (or even barter). You likely aren't buying from a store, but a quartermaster or foreperson who likely has none of the items to sell you, but has to buy them off the locals herself. You can get one of 7-12 by successfully begging and rolling d6-1 for quality. They've got about 50 gp on hand.
Treat wandering salespersons, swamp-witches and members of less reputable guilds as having d3 of items 1-6 for sale, but they don't "use up" what they've got for sale and they likely have d2 of a single uncommon item for sale (roll d10+6 and consult the above). You can probably get items 7-12 by successfully begging and rolling d6-2 for quality. Alternatively, you might get a magical (ahem, cursed) item, depending on the vendor. They've got coins jewels, gems or jewelry worth about 200 gp squirreled away for exchange.
VILLAGES AND TOWNS
You ought to be able to find and buy anything from 1-16, however:
9-12 are available for sale in limited quantities (if you're in a Village, there's one of each, in a Town, d6). The shopkeep knows where you can get more, but you'll have to roll on the quality table (standard roll). You're probably buying Uncle Jed's lantern he's had for twenty years or a cracked and tarnished mirror his wife keeps.
13. Is always available from the local Guild and shopkeeps in more disreputable areas might have one or two "lying around." Of course, asking for them from people that aren't disreputable will prove problematic.
14-15. Are only available from religious institutions, but might be picked up at un-manned shrines (drop a donation in the box), or perhaps purchased from pious villagers (you'll likely need to convince them of your need and demonstrate your association with their deity).
16. Is unavailable in Villages and available in limited supplies in towns. Likely available outside of towns from a swamp-witch or half-man.
All the villagers could likely pool have 100-200 gp, but mostly in bartered goods (grain, etc). Town shops will be able to draw on letters of credit to pay you thousands of gold for stuff. No real concern there, though they're likely not interested in any single thing worth more than about 100 gp.
Work just like Camps and Outposts, but you can get items 1-8 and some uncommon items as a Wandering Salesperson. Might be able to get multiples of 13-16, depending on the nature of the fort, otherwise, there's one of 9-16 with a standard quality roll. Probably have a couple thousand gp to buy stuff off of you, but they're only interested in what they think is important.
Have everything and magical stuff too and you never need to worry about getting your stuff sold.
Note: Rogues in a Guild have access to fences. So long as they can get stuff back to a settlement, they can signal for an occult courier to take good to a fence. The fence takes 5% and the Guild another 15% of the sale.
AVAILABILITY (ARMS & ARMOR)
I'm using B/X here again, but I think the breaking point is obvious.
CAMPS, OUTPOSTS, VILLAGES, TOWNS AND FORTS
A. If the settlement is a Camp, Outpost or Village and local law enforcement is a police body (likely the settlement is unwalled, agrarian and close to trade routes) then anything costing more than 25 gold (Crossbow, Long Bow, Silver dagger, Chain and Plate) just isn't for sale or maybe even to be had by less-than-legal means.
B. If the settlement is Camp, Outpost or Village and local law is generally more interested in defending the settlement than policing it or if the settlement is a Town or Fort (likely the settlement is walled, pseudo-military and further from trade routes or is a town), anything costing more than 25 gold is absolutely and totally unavailable for sale without rolling for quality. Even then, they've probably only got one to spare at any given time.
Have everything and things need not necessarily be subject to a quality roll.
ROLLING FOR QUALITY
A modified d6. You might be able to get a point in your favor if you're a particularly charming or convincing haggler but some places have better stuff than others...
1: Junk. No resell value. If you're playing with these encumbrance rules (part one, and part two), then this kind of stuff is the first thing that breaks. Likely negatively affects reaction rolls if the item is worn or carried regularly (write "Junk" on your character sheet, by your Charisma score)
2-4: Crummy. It works ok, but it looks terrible and is only worth a handful of coin (usually 1 gp for anything cheaper than 25 gp, and 10 gp for anything worth more). Might negatively affects reaction rolls if the item is worn or carried regularly (write "Crummy" on your character sheet by your Charisma score)
5: Well worn. Looks OK. You can re-sell it for half list price.
6: Good. Works like it should.