<p>Definitely apply early. He seems to have great stats for getting a scholarship. If he’s serious about Pitt, have him get all the material he can complete (I.E. essays, etc.) during the summer. He should also contact teachers now that he wishes to have write rec letters for him so that they can start those in the summer or when the school year begins. That way, he can just gather all the materials in early September, apply, and not have to worry about decided last-minute if he can go/etc. (Plus, assuming your S gets in, the financial aid letter comes no later than 2 weeks after the acceptance letter, so you’ll know very early in the year if he can go/if he needs to apply anywhere else or not).</p>