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Old November 3rd, 2017, 03:32 PM
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Difficult question. I think (THINK) that as long as you have your major story points organized, and you know what your player(s) want out of the session, then you'll do fine.

As far as over-preparation, I think two rules apply. First, the players won't take the route you've planned. Second, if you're creative enough you can move any major obstacles to show up where your players go (instead of being stuck where you planned for them to go).
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