That's surprising to me. (Well, depending exactly on what you mean by "one roll".)I've never seen a DM say, "One roll to cross a desert". Crossing a desert is a journey the generally takes days to weeks.
In my BW campaign, the PCs had to travel across the Bright Desert, from the oasis of the friendly naga to the ruined tower in the foothills of the Abor-Alz.
One initial skill check was required: a Songs of Paths and Ways check (which is an Orienteering check, but in the form of an elven Skill Song, meaning that it is very slightly buffed) from the elven ronin PC. I also required each player to make a Forte (=CON) check against a moderately high DC (Ob 4, from memory) to see how much temp Fort lose ("tax", in the terminology of BW) was suffered.
Had the Songs of Paths and Ways check succeeded, that would have been it. It failed, though, which led to the fouled waterhole and out of that the initial altercation with the dark elf. Another Forte check was then required before getting to the tower, plus the failure on a Tracking check against the dark elf meant that when the PCs got to the tower the well there had been filled with rubble by the dark elf (at least, that's as best I recall it - the well certainly was filled with rubble, and I think it was the failure at Tracking that was the trigger for that).
In my 4e game, when the PCs had to fly their Thundercloud Tower down the Obelisk of Ice and across the Elemental Chaos on their way to the Demonweb Pits, that was resolved as a Complexity 1 skill challenge (I think - looking at the date of that post I linked to it was over a year ago!, though it seems like just the other week) which is only a handful of rolls.
Also in my 4e game, the 41 day travel through dozens of layers of the Abyss, from Thanatos (300-ish?) to The Barrens (100, I think) was resolved in a couple of minutes of narration by me. I think there was some sort of check involved in the larger context of a skill challenge - again, my memory is a little hazy - but it may well have been an auto-success for the invoker/wizard PC, who can't fail an Arcana or Religion check except in very unusual circumstances (due to very big bonuses, including the +6 buff from being a Sage of Ages).
Going back to my BW game, we resolved 2 years of recuperation and study in the ruined tower in less than a session. (The main rolls required were upkeep rolls, which is a BW mechanic designed to force the players to make hard choices between doing the training or studying they would like, and doing fairly mundane work to maintain their standard of living - these rolls are generally one or two per season for each PC.)
In general, I don't find there to be any necessary correlation between the number of rolls required as part of resolution, and the ingame arduousness or time required for the task at hand.
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