Great conversation idea and observations! I think Journey of the Brave will most likely come before LBT 14 since it's clear that Bron visited the Great Valley multiple times before Big Longneck Test. Plus, if they're going to show how Chomper and Ruby came to the Great Valley in Journey of the Brave, it would have to take place before the TV series since Chomper and Ruby are already well-settled by that point.
On the other hand, it doesn't seem as though Shorty knows Chomper very well though -- at least, he didn't know what Chomper's diet was, since he said, "I can't go on an adventure with someone that eats like that," after he saw Chomper eat the stinging buzzers. So maybe Chomper and Shorty didn't meet for very long, or maybe Chomper didn't eat while Shorty was around? In any case, it appears that Shorty and Chomper probably didn't know each other very well considering Shorty's reaction.
Maybe Bron will say something like, "I'll see you soon in the Great Valley," at the end of the movie, and the TV episode could be an instance of that. A little side note here, if I recall correctly, this is one of only two TV episodes not released on the 4-episode DVDs, and the other one, The Hidden Canyon, was put on the Wisdom of Friends DVD. It seems like The Big Longneck Test would make a natural bonus feature for Journey of the Brave, particularly if Journey of the Brave comes first, in which case Big Longneck Test could serve as sort of a mini-sequel to it.
