It wasn't a cakewalk trodding down the mountain.
On the path down, Aaron encountered a lot of monsters, Frost monsters like Frost Fox, Frost Tiger, Frost Bear, etc... and they weren't weak.
The teleportation directly sent him to a place with powerful monsters. This is both a good thing and at the same time a bad thing.
It is a good thing because he can hunt powerful monsters and get a lot of tokens placed around, but what colour token he would find or how many he would be able to find out depends on his luck.
The academy has already informed them about such a stage. Though the alliance would not always follow what they did the previous year, with so many years and tournaments passed by, the stages of elimination were all used.