Originally Posted by
wumpus
Note that "free form" and "open question" depend a lot from the player. If a DM gives them the choice between "city A" and "city B", it isn't clear if the DM should reward a player for metagaming the source of the names with a slightly better city. It should be clear that if they are looking for a specific thing and did some sort of research (divination, bardic lore, gather information, hire a sage) to determine the better city they should wind up in the "better city" (assuming they got a good roll on the information source).
Should a DM have an answer to all possible outcomes? Should a metagaming player be rewarded for guessing many of those outcomes? And how much should a DM railroad to avoid forcing the players to make choices without information (that would still require them to have "agency").