I am glad they hired someone with this kind of experience. He does need to get out and talk to or survey average users. His priorities should be:
a) Get the commuter trains moving. It takes 1 hour and 15 mins on an "express" train to go 30 miles on GO Transit. That's not even in the ballpark for a service standard. It should take 30 minutes or less for that trip.
b) Automate the system as soon as possible. He could then run more trains, more often. 
Point A could be fixed immediately, automation will take some time.