It's the definition of a good idea, god awful execution. I have no issue with big/goofy challenges, but the mechanics/rails are so finnicky that it's basically impossible to do this consistently. I managed to do it earlier in the season but only after struggling for an hour or more and it sucks even more the second. Either I fall of the rail for no discernible reason, or the transfer doesn't register for no obvious reason, or I tap B to get out of a grind to roll over to the other side of the rail and I just sail completely off the rail, or I'm apparently going too slow to make it to the far end even though I've been 5-0ing/nose grinding almost the entire rail, or I fly off the rail coming back because when I exit the grind with B my character flips out and does a freak 180 instead of just dismounting, or I get to the very end and the game flips out when I do the ollie on the ramp and my character immediately bails inches from the last bearing. Trying to do this challenge makes me want to uninstall the game and never come back and I've been playing skate games since the very first one. It sucks. Period.