No, I haven't actually had any contact with the OSR's patron saint of gonzo, awesome, fun-maximizing gaming, but he did post this a while back. (The next time I'm in Indiana, though, I'm totally taking him up on his open invitation on the side of his blog to contact him to see if we can do some gaming. Besides enjoying myself immensely, I bet I'd learn a whole lot.) It's twenty questions to answer for yourself when you set up a setting for a campaign, because most of these twenty questions will be asked by your players, and you better have an answer for them.
Almost a year ago now, I started my Skype campaign. I had to toss most of the prep work I'd done, though, and run things on the fly because the player make-up of my game wasn't what I was expecting. I had been expecting to put together a group of friends locally that I hadn't run many games with. Instead, I ended up running my Skype campaign with friends in other time zones who I had run most of the modules I'd placed throughout my map for, so a lot of prep went out the window and one-page-dungeons saved my skin. I haven't been satisfied with much of the world outside of the adventures players go on, though. My NPCs are lame, mostly because I run them on the fly, without planning them out. My economy is ridiculous- I don't have one really good price list, though I'm familiar with several- I just haven't adopted just one, and I'm especially not sure how to present my players, who don't have many magic-using characters, with things to spend money on, seeing as they aren't into the whole carousing bit (and it's not like I've really encouraged them to carouse either). Yes, I'm hoping Adventurer Conqueror King will be especially helpful in this regard.
What I guess I'm saying, then, is that we're having a lot of fun in the dungeons they explore. We've got that part down (especially if I can get my megadungeon expanding again…), but whenever they go back to town there aren't any NPCs they care about or find interesting or really want to get revenge on or whatever, and buying things, especially with large sums of cash, tends to be a stressful event for me and a frustrating one for them.
That's where Jeff's questions come in. They give me a good start in building a world "outside the dungeon," to quote Rob Conley. I'm going to start tackling them one by one, but with a twist: I'm going to try to provide as many answers as I can that can be easily and quickly inserted into many campaigns. I'll choose one answer each time for my Skype campaign, but having other answers ready will allow me to have this part of campaign prep done whenever my next campaign rolls around. Hopefully it will also make these posts more useful for you as you read these.
One last thing: I'll be tackling these out of order, as my muse leads. We'll see how this goes!