I don't know about your son in particular... I'll leave that to someone more experienced! But, I did want to comment on math speed drills (but not get off subject on Mam's post).

I give my kids timed math fact drills (we homeschool) because I want them to have the answers automatically. At first, I resisted giving timed math tests because I didn't want my slower-writing kids to become anxious and dread math. So, what I did was give them a page of super-easy drills (for multiplication, the 0s and 1s page), told them to work quickly, and timed how long it took them to complete it. Then, I doubled that time (because future timed tests would have double digit answers rather than single digit). That time was then their "target time" for all future timed tests. For us, having individualized target times was a lot less stressful than saying everyone has to do 100 problems in 5 minutes.