You're not alone on the Anxiety Train with your 2014. The majority of baseball family's are struggling with the same issues that you are. My son graduated HS in 2011, and I remember the rollercoaster ride that we were on as a family prior to his commitment.
I agree with the majority of everyone else that your son SHOULD BE filling out all questionnaires himself. If help is needed, of course, it's your responsibility as a parent to guide him. My son filled out every questionnaire (college & professional). I made photocopies and kept them in a folder. We kept all written correspondence (email copies & direct mail) in order with each school. The order was based on the universities apparent interest in my son, and his top choices. I helped him formulate a contact list with emails and phone numbers for area coaches/recruiters that had shown interest. Prior to upcoming tournaments, I'd help him put together emails that went out to 15-20 coaches on his list. I helped with the first, and it was his job to change the name(s) on each subsequent email that went out. He answered each & every correspondence on his own. Now, because he was 17-18 years old and didn't have a good grasp on his email account, I admittedly baby sat his email account for several months.
Everything changed on July 1st prior to his senior year of HS. Obviously, that's the date that coaches can contact players by phone directly. Teenagers are extremely comfortable with their cell/smart phones and 247son is no different. Coaches were calling & texting him directly, and I was happy that he had no problem checking his texts, etc.... However, the next few months was sort of a Double Edged Sword, as he continued to receive calls/emails from several coaches, but nobody was pulling the trigger. In the meantime, his friends/teammates were committing to schools. Yes, we were very happy for everyone, but you do begin to wonder when/if your son will get an opportunity? Plenty of Anxiety indeed.
The Good News for my son is that he had a tremendous showcase tourney in front of several decision makers three weeks prior to the early signing period. A few of the coaches on his contact/wish list were in attendance, and the following week our family went on a few official recruiting trips. 247son committed about a week prior to the early signing period.
I'm not going to lie, it was stressful. With that said, it was well worth the ride! It's important that you take a deep breath and enjoy everything, because before you know it 2014 will graduate HS and be off to college....Time Flies!