Austin, your post really takes me back.

dd (now 5) had a number obsession for the entire year she was 2.

In fact, she only wore shirts that had numbers on them (and, yes, my sainted mother sewed different two, three or four digit numbers on to each one).

When I would take her to the library, she only wanted books with "Big Numbers." 1-to-10 wouldn't do, nor would 1-to-20.

I'm trying to remember what we did for videos. I know School House Rock has several songs/videos that are great for skip counting (ie "3 is the Magic Number"). I don't know if that would interest your son...