Thanks for all the thoughts!

blackcat- my ds did use timez attack a bit. However, it usually ends in frustration because of speed, finding the number, and typing it in. Since he feels he's bad at math, he assumed he wasn't ready/too hard until it profiled in his Compass Learning profile.

lovemydd- I really like all those flashkid books. I should look through what I have.

Loy58- How you describe your dd sounds very similar to my ds. I identified with much of what you wrote.

He doesn't want to "fail" by not knowing the answer.( Actually, his high math group is all girls and him.) he also rushes through his work and doesn't want to check for easy mistakes. Hopefully, we can help him feel more confident while still have fun learning:)