Matt,
I agree with everything ILVBB, Strained Oblique and #1 Asst Coach have stated. They've offered you exceptional advice. They've addressed the what and when.
My two cents of unsolicited advice.....I'd like to address "the who". Another point that I think you need to understand as you take this recruiting thing on is that nobody knows everything and nobody is going to work harder at this than you and your son when you understand the options. You mentioned a "recruiting coordinator". I'm not sure exactly what that means. Is this somebody you've hired to collaborate with you or someone that is doing this for you? Here is my point....college recruiting is a tough gig. Very few completely understand what their son wants and what their son is capable of. If you are collaborating with someone make sure they understand exactly what your son is looking for. My son's travel coach was very instrumental in opening some D1 doors in our region and my son eventually getting offers from a handful of D1 schools because of that travel coach. What we learned is that his travel coach's network of college coaches was limited (by region and scope) and there were other options out there that we didn't know about that we uncovered on our own. My wife and I read numerous books, talked to people, read blogs, and did everything we could possibly do to understand the college baseball recruiting universe based on my son's ever changing requirements. Here is my ask....immerse yourself in this process to the point where you are reaching out to college coaches that your recruiting coordinator is not. Keep him updated on your activities and successes, but please take ownership of the process. HSBBWeb is full of people like this and their successes are everywhere. I hope you understand what I'm saying. If you have questions, please PM me.
Good luck!