I would much prefer starting with a used cam and lifter set which wore into each other in the same engine they're going back to. You said you liked the cam back in the day. Yes there are many more modern cams with faster lifter acceleration giving more area under the flow curve BUT the money wasted on a new cam could be put to better use, while eliminating a potential problem breaking in the new cam.

If you search for my handle and .509, you will see that I don't think this cam is all that wonderful. But it can be changed any time. It's a lot easier to swap cams than it is to pull an engine out of the car and clean every oil passage So keeping the current cam is a no-brainer for me.

I agree that the valve guides won't leak around the guides. I have seen similar cracking on heads that were rebuilt. IF you must use stock heads, scout around for a pair of 452 heads, even 213 heads. These are later heads with induction hardened valve seat areas. None of the 440 heads flow sufficient air for a 440 or larger high output engine. There is very little magic in 906s. They came on every bigblock, even the two barrel ones.

I think you're on the right track. Stock crank, stock rods, newer lighter pistons. Stock type heads. Don't pay much for the head cores, they have value decreasing with time.

Lastly, every kid wrecks his first car. It's a truism, but it is based on fact. So he drives carefully. How about with the car loaded with kids chanting "Floor It, Floor It, etc." I'd go a different route. A Hyundai Elantra, 10 years old, or so. They are like anvils, you can beat on them. They are quick, 0 - 60 in less than 8 seconds. I got my 2007 for $3700 two years ago. My car had 91K miles, I'm now at 141K and expect service until 250K. I may have to replace the clutch before too long. You'll do what you want, but be mindful about it. I'd say to the kid that if he can drive for two years without a single ticket, he can drive the Charger.

Good Luck,
R.