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My son never skipped a grade but was placed in Alebra as a fifth grader. While school placement is OK, we find that he needs additional challenes to really stay interested in math.
Look into www.artofproblemsolving.com , they offer classes as well as excellent books that your mentor might want to use.
An interesting way of exploring math is through solving problems from different competitions. You will find tons of old problems posted online. I am against using a formal textbooks for working with a mentor.
We have also worked hard at starting a math circle at a local university. I am thrilled to report that our efforts have been
succesful and today is the first meetingfor the kids !

I would agree with Ania about staying away from formal text books. If your child is on the verge of being turned off by math, then you don't want to just give him more of the same. Math can be very playful and most of the true mathematicians I have known love to play with ideas as well as numbers. What it seems like one would want is to have a mentor who can help introduce a playful element to math (something which most elementary school teacher leave out, often because of their own insecurity with the subject). Real world problems and puzzles (especially ones with multiple solutions) would be a good place to start.

((applause and wild foot stomping cheers!!!!))
CFK, I'm so glad to hear that your DS is excited about the tutor!!!!
Smile,
Trin