Welcome to the forum. We can always use fresh eyes.
I was Jason's Neighbor at the time he disappeared. While the area is not West Omaha, in 2001 it was not the gangland you describe. The Vaughn family of Holy Name spent many years and $$$ buying, renovating, and reselling houses to young families in the area to keep it from being blighted. Even if you watch Omaha Scanner (Facebook/Twitter) you won't see much crime activity in 2022 in this area. Most of it happens on the other side of Fontenelle Blvd. (to the East about six blocks)
Six blocks isn't very far, but the gang violence I am familiar with is drive by shootings, black on black, and nobody is picking up and hiding any bodies. I'm not saying it isn't possible, but we felt pretty safe there. My son also walked to Benson High, and Monroe Jr High before that. He and I have talked about the path we think JJ might have taken. How likely it was someone could have encountered trouble without a neighbor seeing something, etc.
I don't have a favorite theory. None have any evidence. I used to believe JJ ran away, because I was aware of some tension between him and his father over possibly joining the seminary, and I don't even know if that story is true. The longer he remains away, the less likely that remains a possibility. That would be quite a secret to keep.
Anyway, I know some of us have challenged your opinions, but opinions are welcome. I believe they all need to be looked at.