<p>If he feels he could qualify for NMSF, then he should take the PSAT in junior year; that's the only one that counts (unless he plans on graduating early and signals that on his sophomore year PSAT).
As mootmom explained, after he takes the PSAT in October, he can take the SAT in January, March. of May. I would reserve June for taking the SATIIs. Most colleges require only 2 SATIIs (that is, of the colleges that require them at all) but a few require 3, so plan accordingly. Again, the best time to take a SATII is at the conclusion of a class in the subject.</p>