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Welcome, 97sdad!
I may can help with part of your questions.
If you participate in a Perfect Game event a "profile" is created for the player. You can check on your player at www.perfectgame.org and search (type in his name) in the block in the top right where it says "type here". You can check on all his teammates, competitors, and any college and mlb players that participated in Perfect Game events.
It is the parent/player's responsibility to keep the profile up to date with height, weight, coaches phone numbers, contact information, GPA, college commitment, etc.
Since your son played in a WWBA event, which is a tournament, he will not get a rating. You get a rating by participating in a showcase. On the PG homepage, you will see Tournaments and Showcases listed as tabs at the top. PG may make a comment, or a report, about players and the links can appear on the profile.
I only have the free account with PG (just sign up), but subscribers can see rankings for players in most all age groups. Not sure if the 2016s are ranked yet, but if not, they will be soon. Top players will be ranked nationally, by state, and by position.
As for what to participate in after your sophomore year, there is no one "right thing to do". Hopefully your son's travel team will get to the WWBA in Marietta, Georgia, which is a highly respected and scouted event. Of course, there may other events in your state that are also well scouted. If your son is a very good player, he may want to participate in an PG individual showcase to get a rating, or, to get an idea of which college levels he should target. At this point, it is important to get in front of college coaches, rather than playing in tournaments just to win a trophy, if playing in college is the goal. The coaches need to see your player play.
Personally, the summer after sophomore year/before junior year was a critical summer for keewartson. He got on the radar his sophomore fall with several colleges and again during his sophomore high school season. He verbally committed during the summer before junior year. The recruiting time table could be different in your area. Different colleges recruit at different times (D1 before D3 typically). And, typically, up-the-middle players are the first to be recruited (pitches, catchers, mid-infielders). Good pitchers are always in demand, and if you hit bombs, well...you will get noticed.
Is your player high academic? Check out the Stanford Camp and Headfirst Showcases.
Read a bit (alot!) on this board. Do searches. And keep asking questions!
My experience so far has been that talented pitchers will always get seen. My guess is based on what you described you should worry about development and keeping his arm healthy and not be too concerned about the quality of team he plays on if it is at the right events. He will get seen.
Good luck.
Regarding next summer's WWBC in East Cobb, your son should try to work with the team manager to prepare. It will be helpful for your son to know his pitching schedule at least one week before the tournament. He should identify colleges of interest well ahead of time, and invite them to see him pitch. If your son's team is weak, and he's the ace, he should pitch against the best team in the pool. If the manager wants to use him against a weaker team just to win a game, your son should talk to him about his recruiting goals. Those top teams always have college recruiters at their games. If he shows well against top competition, he will get noticed. His velocity will also get recorded on his PG profile, and for a RHP that is extremely important. Also, keep his ht/wt updated on the profile. That's also an attention getter.
As far as "rating", there are many, many posts on HSBaseballWeb about PG "rating/grade" vs "ranking". I can see that PG has published some rankings for 2016 players. Your son doesn't have to attend a PG Showcase to be ranked.
I'm also new to this website and glad I stumbled on it as well. The advice obviously comes from years of experience and passed along generously. Great forums! My son is a 2016, recently ranked by PG. I'm not sure how PG can possibly break these boys out so early, but it was a pleasant surprise to see his hard work validated on the PG site...probably more for me than him! I'm happy that he keeps it all in perspective. He knows there is a lot of work ahead and to just keep grinding.
Someday I hope to be posting the sage advice in these forums. For now, reading and absorbing various opinions and insights is very helpful. As "floridafan" suggested, I'm going to enjoy the ride!
97sdad and Cali2016,
Welcome. "Enjoy the ride" is correct. I'm just about to start my third ride with son #3. I'm putting a seatbelt on this time.