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As many people as would like to can join in -- they'll just have to use a bit of their ink. Since he's the one using all of his ink to conjure the vision up, it won't take all of theirs, just about half. If they don't join in with his vision then, though, he'll have to exposit it on them!

The landmarks are very distinct, so while it may take some time to find one of them, once he manages to do that he'll be able to follow the right path properly. Imagine stumbling around the woods for hours upon hours until he finds a large, strangely shaped rock covered in mysterious moss patterns. Once he finds that, he'll know he's on the right path, and then the path will be just as he saw in his vision.

It may take trial and error, but if he works at it, he'll manage!

(As a hint, the path will be much easier if he brings people of many colors that he has strong bonds with.)