Your plans sound perfect and I highly recommend the adventure. My then 15 year old and I made the trek in the 59 from May to July 2004 and had a blast. He'd just gotten his learners permit and was a big help with the driving although quite nervous driving the truck. Had to feel for him at the end of each day as he was beat down good and ready for only a hot shower, dinner, and bed.
Take lots of pics and as Jed says sounds like a great experience to document.
