Staying at the Stoop certainly does help to be in on the plans, but I remember one night we had 2-3 trail options we were discussing at midnight and I don't think we really settled on one until the next morning as we were lining up to head out. Personally though, I enjoy that style of organization (or lack there of) because like others said, I'm on vacation and its way more fun and spontaneous that way.
As for trying to figure out what trails to run and with who, that's one nice thing about the big beginner run on Tuesday to feel out how your rig and driving abilities line up with others so you can find trail buddies. I mostly stuck with the same group all week, running a few trails with Mark, Kat and Jon. I had it easy because, while I don't have much trail experience, I have a really modded truck so my driving experience was my limiting factor and not my trucks capabilities.