I sent him 3 times to the valley. The 1st time is the only one rough. You only going to see the most effect in the end of this 0.3 update after get the wine. I think. (Maybe I played Echo too much and end insane... =@.@= )
But I saw 4 different versions of it depending of how many times you send he out and when.
You will lost medals in the like record showed in the end of the last update for each time you sent him to the valley.
Remember that you have different reactions from the snack guy too if you get the right artigle and some other stuff right It is kind comical.