Yeah, I never considered the Tribeca. The Outback seems to be tried and true, and if he's just going for 5-seats max, the Tribeca just reads fail.
I do like your Honda Pilot and I really like my friend's Honda CR-V. I also like the Toyota RAV-4. However, excluding Tribeca quirks, it's tough to pry away from full-time AWD for most people.
Pilot/Tribeca/Outback sizes might be overkill for him. Forester might just be the biggest I'd recommend for retaining that sporty feel while driving.