Gotcha. D&D is my background, too, but even then I think more of Insight or Sense Motive, depending on edition. No worries, though.
You're probably on the right track with the questions you're asking. Personally, though, I'm alright with not knowing everything before we go. I like to learn on the fly sometimes. And no, it doesn't always work out in my best interests. :-)
For me, nailing down every single detail before a run is a lot like searching every foot of every hallway for traps in D&D. It's probably the best idea, but it feels overly paranoid sometimes. I'm fine with someone in the party doing these things, but they aren't where my mind tends to go. Just not my playstyle.
That said, I'm very happy to have the analytical, cautious Twisted Sister filling that role for us.