Im glad to see you ride often. Trips like this are not simply a matter of I have ridden for years.....
If you are not used to 400 mile or 8 hour rides, this is very ambitious. Count on at least 20% longer times riding than any maps tell you it will be.
10 hours in a car is nothing. 10 hours on a bike back to back are long days.....
Uhh he's 28, I'll bet he can handle 12-16 hour days day in day out. I can at 48.
Well, I'd respectfully suggest that few can at any age if all you've ever done is bar runs or a few hours every other weekend. It's just advice from someone who has done a lot of multi-day trips, take it or leave it.