I had always kept Pebbles in a shorter cut but decided about 6 months ago to let it grow out. It's still wavy but as it is getting longer it's beginning to straighten out. I noticed the other day on FB that Jackson's hair was getting long and I thought he looked adorable. But~the longer hair does take a lot more maintenance. With all the activity that you and Jackson like the shorter cut is probably the way to go. Just a side thought....you could let his head hair grow out and have the best of both.