The first time I caught air in a pickup I was 16. I came very close to going end over end. Just sayin' ...Coming from boy's experience also, you should plan on the first vehicle they drive to be a crash test dummy. It WILL NOT survive no matter how hard they try My kids are very, very good as well and both have been driving for years on motorcycles or gravel roads growing up but, mix testosterone with peer pressure and crap happens. Just pick something slow enough at first that crap doesn't happen at supersonic speeds. Get something expendable at first for practice, then move up. When my son had his first accident no one was hurt and I wasn't mad, he had been driving for years and honestly, I expected it much sooner but I thought he was safe and out of the clear. So, we got him a much nicer car for a graduation present and shortly thereafter it was wrecked.
I wasn't mad because it was his first accident but he was devastated because he thought "mom and dad gave me this beautiful car and I wrecked it". If it would have been some POS he wouldn't have been nearly upset but he thought he had let us down
I am also talking with a well known local builder to see what options he has. Any weak parts in the transmission that I should look at? Either way I'm having the transmission refreshed and was considering a 3000 stall converter.I assume you have done plenty of research on the 6.6 before dropping the $$ for it, but I personally would be saying 6.2 and just have the engine rebuilt with forged internals and plopping the Whipple up there. Not throwing stones at Livernois but the gain of the strokes 6.6 does not outway the reliability and cost. One of our Raptor brothers here in TX had a nightmare with his and it broke, then never ran right. (Livernois build, Livernois tune)
Take a look at Cody Dawson or Bobbelheads builds if you need to see what parts you need.
Having had a supercharged 6.2 with a good tune, I had no issue making the 6.6 look like a ****.