To give you the short answer - Nov to May is not recruiting time.
I'm sure you'll hear a story or two about how some kid went to some indoor showcase, killed it and some schools showed interest. But for the overwhelming majority, the months leading up to the season and the season are based around the actual team, not recruiting.
After NLIs coaches can breathe for a but before they determine who is getting let go at Christmas.
You can play the what if games/what are the odds as much as you'd like but the advice is going to be the same almost all the time. If your kid has an offer that he likes from a school he'd like to attend then jump on it. If he doesn't want to play at that school or wants to hold out to play at a higher level he can try, but if it doesn't work out don't expect the first school to be waiting with open arms.