I would be very careful about a two grade skip at one time. Your DS scores are very high. However, you are talking about putting your 8 year old in the 5th grade and there is a lot more to school than academics. Will he end up being the "baby" of the class or do you think the other 5th graders will accept him as a peer (both in and out of the classroom). I might advocate for one grade skip, see how it goes and then decide later if you want to try for another. Also, we are considering a grade skip this year (1st to 3rd) and someone on the board suggested the Iowa Acceleration Scales to me. We used it and it was very helpful to us in making the decision. Best of luck:)!