I’ve never played Burning Wheel, but I’m going to try to translate what I think “Let it Ride” and “Make it Interesting” mean into D&D with a familiar scene:
The Fellowship is trying to cross the Misty Mountains at the pass of Caradhras.
The party has on their side several hearty adventurers including one very skilled woodsman, a wizard master of fire, a fleet-footed elf, and several tough, but not particularly useful hobbits. They are not well geared for the climb (Sam didn’t bring any rope), but they have plenty of cold weather gear and have brought along plenty of firewood (thanks Boromir).
Everyone makes a CON check to endure the weather. It gets really cold and starts to snow heavily as they make their way up the pass. Anyone that fails the check will suffer some damage scaled by how badly they fail and mitigated by any extra precautions or efforts they use to defend against it. This damage will occur periodically as they continue the journey using the single check per character.
The most skilled in outdoor survival (Aragorn) makes a WIS check to find the best path. They WILL find a path across, this check just determines how long it will take, and how many times they suffer damage from the cold. Lack of proper climbing gear impedes this check.
So, they’re making their way along the pass. Everyone makes a CON check: Boromir, Gimli, and Gandalf succeed. Legolas does too, mostly due to his elven adaptation (Tolkien elves are like little gods, you know). Aragorn fails marginally. The four hobbits each suffer varying degrees of failure with Frodo faring the worst.
Aragorn finds a path, but it’s not a particularly good one, and this trek is going to take a very long time. Damage starts to accumulate from the cold and the snow. Eventually Boromir points out that the hobbits will die if they keep on, so they decide to stop for rest and start a fire for warmth.
Gimli can’t manage the fire starting (WIS check failed), so Gandalf lends a hand. Gandalf can automatically start a fire using his magic, but doing so alerts the giants living above the pass. The Fellowship decides to wait out the storm and look at moving forward in the morning. The fire mitigates much of the damage from the cold and only Frodo continues to suffer. Everyone takes a sip of miruvor (minor healing potion) and recovers some strength.
In the meantime, the giants saw Gandalf’s fire and start dropping boulders down around the heads of the Fellowship. This disturbs their sleep (no rest tonight) and has a very small chance (easy DEX check for each character) of doing some traumatic damage if someone gets hit. Luckily no one takes a stone to the head.
In the morning the Fellowship assesses the situation: the pass is blocked with snow in both directions. Legolas the super nimble and never daunted (damn Tolkien elves!) leaps up and goes to check things out. Making a WIS check he determines that it will be easier (though not easy) to turn back than to press forward.
The strongest member of the party (Boromir) makes a STR check to clear a path back down the pass and Aragorn assists. Again, success is guaranteed, but the higher the roll the quicker he can make way for the hobbits who continue to take damage from the cold, though the damage is less now as it’s not as cold and the snow has stopped.
The Fellowship makes its way back down the pass having failed to cross the pass of Caradhas with several folks suffering some frostbite and Frodo in pretty bad shape. Another sip of miruvor and some rest and everyone’s ready to try the Hollin Gate.
They could try the pass again, but they’ll suffer the same bad result unless they can come up with some good climbing gear, find a good map of the place, or otherwise change the situation. Weather control might be nice!