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I think everything you're saying is a possibility, even strongly likely. But I disagree that it wasn't impulsive. IMO, the purpose of the meeting was something other than murder. I know it wasn't baseball season, but the killer could have been coming from a practice or tryouts or something like that. He could have been enraged when the bat was already in his hand -- a weapon of opportunity. Henry having the personality we've discussed, he could have antagonized the killer, not even thinking he'd get hurt. I don't think the killer was thinking that far ahead in bringing the bat as a weapon or protection. If he had, he would have taken it with him.Along those same lines, the person who did this had some severe psychological problems to kill Henry in the first place. Those psych/mental issues were in operation before and after the murder and allowed the killer to feel no guilt about what he did. No conscience. Maybe he was used to not being held accountable to others.
For that reason, JMO, it's likely this killer stood out to other students in school and around town. Maybe not in a big way, but I'd be willing to bet he was someone known to have a temper or to bully others. If he came from a "good" family, his behavior may have been overlooked or dismissed by others.
Another possibility is that he was considered an oddball or loner, someone whose violent tendencies were not obvious due to social isolation.
Regardless, he was a schemer. He was someone who took the time to arrange a place and time for his meeting with Henry and bring along a weapon.
He arranged it in a way that didn't arouse suspicion from Henry.
He was organized enough to escape unnoticed and dispose of evidence (bloody clothes, etc.) before cleaning up and returning to "normal", not an easy task for a minor who still lived at home with his parents. Are we looking for someone whose parents worked and weren't usually there when he got home from school?
Henry's murder doesn't appear to have been an impulsive act, it was planned by someone who could trick Henry into going to that spot that busy afternoon.
Just a hunch, but I suspect some friends and fellow students of Henry's had or have suspicions about the killer. For various reasons, though, they rationalized that it couldn't be him.
JMO
I like what you said about the parents working late. Just wanted to highlight that point. If the kid lived in the neighborhood, which is most likely IMO, it's a bunch of duplexes that may attract lower income families than the rest of the town, parents working late, working multiple jobs, or a single parent are great suggestions about his home life.