Baseballmom2013,
If as you say you are overwhelmed, that to me is a good sign that you may want to at least talk to an advisor. Once the game of baseball becomes the business of baseball, it is worth having someone who is educated and knows the business on your side. You owe them nothing and assuming you can get the right person, you can gain a lot. I am not familiar with MLB teams frowning upon this. They deal with plenty of advisors so if you select one, you join the thousands of others that have done the same over the years.
You may invest a few hours interviewing a few firms to find the one that clicks with you and your son, but in the end those few hours are nothing compared to the peace of mind you have knowing someone has your back and the education you can receive about what to expect.
My best to you in the process.