Any negatives?

Based on what you've said, I'd definitely go....doesn't sound like a big amount of $$$ and with his size/velo, it can't hurt to get him in front of the coaches.

root,

My son is also a 14yr old freshman (late june Bday)...he attended a college prospect camp a few weeks ago and loved it...he was one of two 2018's there and had an opportunity to talk to the coaches and get a feel for the atmosphere.  He's a little over 5'10 140pounds so not your sons size, but the coaches still took notice when he was swinging the bat and pitching...he received the "your only a freshman?" look and response on a few occasions...i could only imagine what they would think if they saw your son.  Good luck and let me know how it goes!

Is he prepared to handle himself properly if things don't go well on the field?  Is he prepared to throw against 16-18 y.o.'s?  If yes to both, probably a pretty cool thing to do.  The only other thing that comes to mind is that it would be nice to have a few of these events under his belt before attending the one at his dream school so that he is comfortable and familiar with the format.

I'd go.  With his size, he has the "eye candy" factor.   His velo should be fine for playing against older guys.   

My son participated in Top 96 when he was 14 and did well.  It was a great chance to meet some coaches, send thank yous, and get on contact lists.

Even if he does not do well, the experience will be good for him and prepare him for other events.

Has he attended any kind of a showcase event just for the practice and familiarity with the process? If not it might not be a bad idea to do a cheap local one first. I realize local is a relative term based on where you live. The only issue would be potential nervousness having a first showcase be his dream school. But regardless of what happens I would think size and velocity at his age would get him on a watch list. He should understand at his age it's more about appearances than actual results. He'll be facing far more experienced hitters than he's ever seen.

What kind of throwing shape will he be in when November comes around. Will he have been pitching up until then? Will there be arm fatigue from a long season? You want him in that 82-84 range when they see him. Would it be better to wait to do this next summer?

My son went to his first "college camp" when he was 13....just so we could get a feel for it.  We took him and another player from his travel team.  These kids were very good for 13U players...but neither was much more than 5'2 or so...and probably less than 100 lbs at the time.  We went the night before...and were just about the first two kids to sign up.  They got in...registered...and stood looking in awe at the D1 field they were going to be on that day.  THEN...the other kids started showing up....wearing jerseys/hats from some of the top HS's in the state.  Big schools...and big kids....lol.   Next thing I know they're standing back against the wall looking like they're trying to sneak out to the car.

Once the event started....an assistant coach from a Top 20 D1 talked to them as soon as they got on the field.  He really seemed impressed...especially after he gave them both a shot at SS against the older kids...and neither of them so much as bobbled a ball the entire day. 

After the event, the coach came over....told me how impressed he was with how they handled themselves...and complimented us on taking the initiative to have them at an event like that as 8th graders.

My son attended quite a few showcase events after that....and I think based on how he did that day, he never once looked even a little bit nervous...no matter who he was up against.

My son is committed to a D1...and the other player will likely play at least D2....though he has the potential to play D1 in basketball or football (which are now his 2 "main" sports).

I would take him....I really think it helped my son...even if nothing came from that day, it was a good "start" and he learned a lot from a bunch of D1 coaches that were there that day.