I think you are making some very valid points. It's a crap shoot as 2 if he will enjoy the adventure or NOT. He may love it or he may hate it or something in between. He won't be able to know, for sure, until he does it.
As far as my possessions go.. I have a love/hate relationship with all my "stuff". I like my home. I like my car.
If Andrew does "The Hike", I believe, it will give him a different perspective on life and everything that goes with it. It could be a very good thing.