>rolling to see if an establishment exists
What kind of shit..?

I usually just come up with something on the spot.
I'll usually throw in three taverns, two general shops, two specialty shops (usually one apothecary and one blacksmith), and one highly influential "guild".

One one rare occasion, I threw in a subplot about two rival candy shops - one with an assortment of candies and pastries and another with a monopoly on the bon-bon industry.

>>46198241
It depends. What is the size of the town? Where is it located both geographically and culturally? What background does the town have? I usually have most of these questions answered before my players enter the town and then pull different establishments out my ass from there. I always keep the basic Tavern/Inns, Blacksmiths etc though.

Sometimes I like to fuck around with players and tell them that each Blacksmith has different stats, they then spend ungodly amounts of time comparing the blacksmith's wears and rolling for investigation/insight to try find the best smith to craft their equipment.

>>46198241
>They want to know what establishments the locale has
Then they can roleplay investigating the town. If they want life on easy mode, they can just say "I go to the nearest blacksmith's shop" (assuming we're talking about medieval fantasy here).

I do have a list of NPC names on hand, so that I can give a name to anybody they interact with. A guard, a prostitute, a blacksmith, their next sworn enemy, or whatever.

Ditto for the names of taverns or inns, since I figure that's the only business that really has to have a memorable name.

Otherwise I just wing it. If I really want a place to have a unique flavor (like a major city at the center of the campaign), I'll come up with several iconic locations, and work a little harder on creating a local flavor.

>>46198241
List for most significant cities/settlements, improvise otherwise.

>>46198362
Also, if the players ask about something I didn't expect, but I think makes sense, improvise. (Like if a rogue asks for the black market in a major city and I hadn't considered that but think it should exist.)

>>46198241
Improv. I tend to assume most towns have some sort of law enforcement, a religious establishment, a number of shops selling generic crap and a tavern equivalent of some sort. Sometimes I take a few off the list, but the nature of the places is always made up on the fly. Names etc primarily, but sometimes customs as well.

Here are two towns that I made in the format I usually work in.

Fishertown
>A lost tribe in the north that struggles with the elements every day. Bone and leather help form temporary hunting camps several weeks out of the year, but the warm wooden lodges are always there.
>Predominantly homogenized half-elf mix
>Whaling, fishing, hunting
>Shamanism

Steelhaven
>Bustling and thriving with the natural industrious inclination of humans, it has grown into a warm vibrant city of stone and steel.
>Capitol
>Predominantly human, few halflings
>Trade, crafting (glassmaking, alchemy, clothing), farming, smithing
>The Ebon Shield
>>“Non-religious” organization devoted to spreading propaganda against things not sanctioned by the Deacon
>The Scarlet
>>The King’s bodyguards

>>46198299
I feel like I recognize that candy shop reference from somewhere...

Almost entirely improv. Obvious inclusions are apothecaries, inn's, tavern's, and grocers of varying size and quality then various random bits like guilds, mailing outposts, stables, blacksmiths, traveling vendors, circuses, farmers selling their wares, etc. whatever i feel best fits wherever they are. I don't do brothels with my current group anymore since they take it too far.

Third option and if the dice say no then I move on to the second option.