So I'm new here and I spent a few hours reading these threads and a few things stand out that I feel were glossed over. Sorry for the long post.
1) An article that came out a month after Jason went missing said that his friends 'haven't heard from him in months.' This strongly implies Jason had already withdrawn from some key "normal" aspects of his life prior to going missing, and that he likely had friends elsewhere that his parents were never aware of. Someone mentioned that they used Wayback to access his college profile and he'd listed his interests as 'Internet' and 'Email.' You don't list your interests as internet and email back in 2001 unless you are using them *a lot* and getting a lot out of them, and he also had a personal computer on which to do so. At the time, i think my family only had one communal one. I know the family and/or LE said they'd looked at the phone and computer, but given that police nowadays can't even be relied upon to know much about online stuff, I really can't imagine they'd have had the knowledge or the tools to access the private online life of someone who had a strong interest in internet and email.
2) Jason's role in his church and religious community. His parents emphasise Jason's faith a lot. Jason did extra hours at the church, did prayer readings, and someone mentioned that his father was leaning on him to go into the priesthood. Now I have experience with Catholics... If Jason had anything going on in his private life that he thought his parents would disapprove of (which would be a lot: the wrong type of music, a boyfriend, the wrong girlfriend, premarital sex, drinking, cigarettes, drugs, literally anything that teenagers tend to naturally explore) there is ZERO chance he'd have been able to let his parents in on any of it. Now here's another thing about Catholicism. You grow up massively internalising guilt and shame, even if you're a "good" Catholic. If you have aspirations to any kind of life outside your family and what your family want – especially if they want you to be a priest – it's very much all or nothing. Just knowing the pressure these communities put young people under to conform, I have no trouble believing that if Jason wanted to live a life that his parents would've been ashamed of he'd feel he'd have to cut ties 100%, because that's kinda what the community demands of you. Wanna do something like be gay or bi? No, you can't tell your parents. Wanna disappoint them by going into the arts instead of into the church? That probably wouldn't feel like an option. Religious repression is real and it fucks kids up. He may have had a strong faith but that may have made everything worse, because he'd be ashamed too, he'd be guilty for having any secret interests or vices that average teen boys have.
3) Only having his parents' account of him to go on. This is where any chance at an accurate assessment of Jason as a person falls down for me. He was nice, shy, responsible, yeah, I have no doubt he was all of these things to the people the police knew about. But we also know that Jason went for long walks for hours!? To the extent that his parents didn't even initially panic after hearing he hadn't turned up to meet his coworker, thinking maybe he was just out walking as he liked to walk so much. His parents don't know where he was during these hours outside the home. They are apparently used to having many hours unaccounted for. Yet, in an early interview, they describe Jason as happy being 'a homebody.' Really? At 19? With an interest in the internet and taking long walks? None of that squares away for me. His parents said he'd been going through a rough time and that they hoped the new job his uncle had got for him in sales would be 'the light at the end of the tunnel.' Strangely enough, the last Bible reading Jason gave at his church was a passage from Romans about suffering eventually leading to hope; a light at the end of the tunnel. Furthermore, even if the priest at his church was told something, or Jason had confessed something secret to him, he's bound by the sacrament not to tell the family. Sometimes priests can go rogue and alert police to actual crimes, but priests and churches have this way of closing ranks and protecting themselves when something goes awry, or might embarrass the community. And Father Vella (?) has since moved to another state.
So, taking all this together. Jason very likely had a private life separate from his parents, conducted via email/internet. He was part of a deeply religious family and community that would give him a lot to be ashamed of if he deviated from their idea of what a good responsible Catholic boy should be doing with his life. All of this could plausibly lead to two outcomes:
1) Foul play theory. He had made prior plans with someone the day he was called into work early. Someone he made a point of not communicating with by phone, so online or in person only. Detoured to meet up with them on his way to meet his coworker (regardless of whether he actually intended on meeting her or not). Could be related to sex, drugs, an older man who groomed him, whatever. And he meets a bad end.
2) Or – and I find this more plausible – he told his boss/coworker that he'd be okay to come in just because he's an awkward 19-year-old and that's easier than saying you won't. He meets up with someone he always planned to meet up with, and leaves town. Purposefully leaves his car, card, documents, all the things that his parents/police would reasonably use to trace him, and leaves to go live the life he wants, likely with the help of someone who said they could help him out with the relocation, somewhere to live/a new job etc. The reason I find the runaway theory so compelling is because even if he did end up contacting his family after the fact, just to let them know he was alive, his family would never, ever, embarrass themselves by telling the police, church, or wider public that Jason was fine and living somewhere else. Na, they'd probably just quietly get on with their lives, move house, let the website expire etc.
To be clear, this is all just speculation, and option 2 could also have led to a bad end. But I choose to be optimistic.
All fresh eyes on JJ's disappearance are appreciated. Based on your comments, I did some quick searching, and Central High School (4.2 miles from Benson HS where JJ was supposed to meet his co-worker the day he went missing) has the Eagle as its mascot. I searched for any murals (the brick wall?) of eagles in the area and was directed to the Blackstone District, where my search mentioned some birds/drawings, not eagles specifically. 
