Greetings Bostonian!
Everybody has shared lots of great feedback. Agree with NotSoGifted... way too much testing and really not needed. Two subject tests should be plenty and I also agree that your son should take them when he has finished the courses or when he feels ready. The pressure really ramps up when they are juniors so think of it as a marathon so you don't want to burn out that really smart boy of yours too soon.

I'm impressed how organized you are and I am going to make you shudder (or probably feel better) when you hear our story. Thankfully my husband found out our DS needed to take subject tests (found out late in our son's junior year). Consequently, with all the other testing and activities going on my DS did not take them till December of his senior year. He did OK (he didn't have time to study and it was too far out from when he took the classes). He could've retaken them in January for some of the selective schools he was applying to but I encouraged him to not retake them. I knew he wouldn't take the time to study so why risk his scores dropping. With all his college apps, college classes (we don't have AP), activities, etc. he was getting burned out.

The good news is that our DS got accepted into Harvard and Columbia for engineering. He also got accepted into other good schools but this is the two he is deciding between. Hopefully this is encouraging to you and that the path to getting in a selective school doesn't require a perfect, straight trajectory. I realize that for MIT and Cal Tech your son is going to need stellar subject scores in math and science but just like the previous posters recommended, make sure to not overdo the testing and take it closer to when he has completed the material.

BTW... have you ever gone to www.collegeconfidential.com? I think you might really enjoy it if you haven't been there. Lots of great specific talk about testing and colleges. Good stuff!

Best to you and that bright boy. Lots of fun stuff coming up!