There are many game designers out there who have said that the modern world makes the best setting because there are no shortage of splatbooks for it. This is true, but it's both a blessing and a curse. When a player is more savvy than a GM on certain things (inevitable in usually one or two things) the GM can feel like his game isn't authentic when the player challenges him with questions like: "Why are these cops following [X] procedure?" or "I just go to [website X], they have all that information as a matter of public record."
If you're a GM that doesn't know the details of how a particular aspect of the modern world operates (say you've never been to prison, so the procedures of prison guards aren't familiar to you), you have a few options available to you.
1. The first one should always be EDUCATE YOURSELF. There are a lot of TV shows with pertinent subject matter out there, especially on the internet. Discovery channel is every gamer's friend, shows like THE SHIELD can show you plausible loopholes in the police system and Burn Notice is a veritable instruction manual on doing sneaky things.
2. The second one is going abstract when you don't know the specifics. You may not know exactly how a police officer interrogates a PC, but you can always gloss over some of it and get right to the pertinent part of the interrogation to see what the cop learns.
I know the hardest thing for me in running a contemporary RPG is how to keep the world sane. Players want to do crazy stuff, but society functions by not tolerating the disruptions created by doing crazy stuff. Whenever you make a scene there needs to be repercussions, but sometimes you as the GM need to let that scene be made to make the game fun, finding that balance has been a trial for me as both a player and a GM, and I'd be interested in knowing how any of your game groups manage it?
There's also the excellent option of asking from other participants. When running a scifi game featuring suspiciously zerg-like aliens I asked a few things from one my players who just happens to study biochemistry as his major.
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