Whether it's a bazaar, town square, or slum alley, you probably need a commercial district in any large fantasy city. Here is my approach to populating that so it seems like a busy, vibrant place instead of one general store.
1. Think of the items you want to be on sale. For example can you buy weapons? Mason's tools? Brewer's tools? Thieves' tools? Magic items?
2. Group the items into related groups. These are not necessarily the same as the groups you thought about to find what was on sale. For example, if you have an upper class neighborhood and a lower class neighborhood in your city, you might put high-cost items in a store in the posh area, and rare and powerful but forgotten items in the slums.
3. Look at your collections of items and think about what kind of proprietor would sell these items. For example, if there are a lot of magic items with a chaotic nature like Bag of Tricks, maybe the proprietor is a goblin or fey.
How to run the shopping trip:
You want to give your players the impression that more shops exist than what you've created in your worldbuilding. So I don't have them pick their way through a pre-defined map and tell them when they come across one of my stores. I just abstract the window-shopping by having a player who wants to buy something roll an Investigation check. They can use Charisma instead of Intelligence if they want to, to model finding what you're looking for by inquiring with locals.
If there are some kind of "underground" shops, they might need to meet a DC to be able to find those shops. Otherwise I pretty much ignore the roll, but it gives the impression to the players that there was something they could have found, but didn't. Then I take the player to what I think is the best store for them. I plan before the session which stores have items that I think my players might be interested in. If they've given me no more information, then I just pick that predetermined store for that player.
Then, once they enter the store, I don't necessarily describe all the goods on offer. Instead they make another Investigation check to browse. The roll is irrelevant and again just gives the impression that there might have been products they didn't find. Then I'll offer what I think is the best item this shop has for that player. Alternatively, a player might ask for a general category of items, such as "+1 weapons" or "potions" or "something to help with strength saves". Then I'll use that to direct them to the best-suited item, or I might even make one up on the spot.
Sometimes, if they socially interact with the shopkeeper, the shopkeeper might even reluctantly give them a recommendation of a different store that has more of what they're looking for. You can ask for a Persuasion check depending on how well they've been reading the shopkeepers demeanor. Some shopkeepers have very friendly customer service, others act like they're doing you a favor by selling these exclusive items. Again, you probably ignore the result of this Persuasion check and tell them where they need to go, because you curated all these cool items and created all these shopkeeper NPCs, and you want to show them off. If they make a medium Persuasion roll, the shopkeeper just gives directions. If they make a high roll, then shopkeeper gives them a password to a secret back-room black market shop. If they make a low roll, the shopkeeper doesn't help, but the store they should check out just randomly happens to be around the next corner.
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Whether it's a bazaar, town square, or slum alley, you probably need a commercial district in any large fantasy city. Here is my approach to populating that so it seems like a busy, vibrant place instead of one general store.
1. Think of the items you want to be on sale. For example can you buy weapons? Mason's tools? Brewer's tools? Thieves' tools? Magic items?
2. Group the items into related groups. These are not necessarily the same as the groups you thought about to find what was on sale. For example, if you have an upper class neighborhood and a lower class neighborhood in your city, you might put high-cost items in a store in the posh area, and rare and powerful but forgotten items in the slums.
3. Look at your collections of items and think about what kind of proprietor would sell these items. For example, if there are a lot of magic items with a chaotic nature like Bag of Tricks, maybe the proprietor is a goblin or fey.
How to run the shopping trip:
You want to give your players the impression that more shops exist than what you've created in your worldbuilding. So I don't have them pick their way through a pre-defined map and tell them when they come across one of my stores. I just abstract the window-shopping by having a player who wants to buy something roll an Investigation check. They can use Charisma instead of Intelligence if they want to, to model finding what you're looking for by inquiring with locals.
If there are some kind of "underground" shops, they might need to meet a DC to be able to find those shops. Otherwise I pretty much ignore the roll, but it gives the impression to the players that there was something they could have found, but didn't. Then I take the player to what I think is the best store for them. I plan before the session which stores have items that I think my players might be interested in. If they've given me no more information, then I just pick that predetermined store for that player.
Then, once they enter the store, I don't necessarily describe all the goods on offer. Instead they make another Investigation check to browse. The roll is irrelevant and again just gives the impression that there might have been products they didn't find. Then I'll offer what I think is the best item this shop has for that player. Alternatively, a player might ask for a general category of items, such as "+1 weapons" or "potions" or "something to help with strength saves". Then I'll use that to direct them to the best-suited item, or I might even make one up on the spot.
Sometimes, if they socially interact with the shopkeeper, the shopkeeper might even reluctantly give them a recommendation of a different store that has more of what they're looking for. You can ask for a Persuasion check depending on how well they've been reading the shopkeepers demeanor. Some shopkeepers have very friendly customer service, others act like they're doing you a favor by selling these exclusive items. Again, you probably ignore the result of this Persuasion check and tell them where they need to go, because you curated all these cool items and created all these shopkeeper NPCs, and you want to show them off. If they make a medium Persuasion roll, the shopkeeper just gives directions. If they make a high roll, then shopkeeper gives them a password to a secret back-room black market shop. If they make a low roll, the shopkeeper doesn't help, but the store they should check out just randomly happens to be around the next corner.