Two things. First, I really do like to roll for characters to know these things - what it means, however is that the player learns the resistances involved. That is, if say the trip is really a long one through territory that the characters know little about, it's fun to have them roll to see if they know what the resistance is. A good success will add a penalty to the target resistance, as the character knowledge of the path is good enough to make the trip shorter. On a failure, the opposite is true, and their travel ability will be penalized (in addition to me not telling them what the resistance is precisely, "Well it's in the one mastery range...").
Again this is all quite realisitic. Ask anyone who's ever done a land navigation course if these things matter to travel time. Or, like you say, knowing the back alleys of your hometown.
Again, the "real" answer in terms of distance is the resistance for the players - that's what matters to them (the leagues only matter to the characters who we can assume now know the answer). And of course it won't change one it's been established. Why would it?
Mike
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