So, here's how Let it Ride worked at our table (well, okay, it was a skype game so there was no table but such is life):
The orc are traveling north to the Seven Kings Mountains, where a dragon has a horde of orc as part of her armies. War is raging between the Dwarven kings and the dragon.
The orc PC wants to somehow get the dragon's orc horde and return to the Broken Mountains with them.
But first thing's first.
Orcwatch is an old elven castle that watches over the orc homelands, the Broken Mountains. The orc have have to make a Stealth check to get by the elf outrider patrols and get to the mountains.
They made their check. They got by and continued on their way to where they wanted to be. My players were a bit shocked by this and I think it was Let it Ride that kind of jolted them a bit. They thought it was going to be rather difficult and honestly, it was a tough roll but they had plenty of helping dice from their wolf steeds and elf-wise.
"Do you guys want to hang out around Orcwatch and do some raiding or something? If you want to take it to the elves, we can roll some dice and play that too but I thought your eyes were northward. I'm flexible; you tell me what you want to do."
They conveyed that they were cool with it, they just thought there would be more dice rolling and that making it past the patrols would be more difficult. It was difficult but it was one difficult roll, rather than several, allowing them to concentrate their helping dice and artha into one effort, rather than have to take their chances with several, in an part of the map where their interests didn't sit.
Mind you, had they failed, they would have met a contigent of orc-wise elven outriders with spell songs and the whole shebang. It would've been no joke and a rough battle.
But they made it past and travelled north towards the Dragon.
