Two things I have been noticing with my friday night game of Pathfinder:

It takes a bit of work to get modern D&D players to get comfortable with gridless play… It took a lot of work to make me comfortable with not having every part of an area mapped out either, but there are many things that work better if we don’t have an explicit map of a whole region (caves, sewers, mazes, the wilderness, city streets…)
Instead explicitly mapping the whole thing, the better solution is to map the important encounter areas. That way you can be a lot more flexible. It is similar to the Dresden Files city building. You deal with entire sections of a city by defining an important area and person that sets the tone. The problem is that since I have a map that is set up in measured squares, certain types of players want the whole world to be measured in the same sort of defined grid.

The other thing, and I love games like The Dresden Files game for it, is that it takes a lot of effort to get your players to make up parts of the world as they need them. I asked my players to come up with a place where they were living and I was asked if I wanted them to read all the books so they’d know what was avaliable in setting… The whole point is that the setting is done in broad strokes and they can make up all sorts of things that fit between those strokes. (Of course, a 1930s style New York Firestation with a giant nuclear reactor in the bottom level? Alas does not fit within the broad strokes of the Eberron setting.

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