Best way to book is a cash fare, they are usually cheap [delta is pretty ok].
Award adds 49+ in fees.
Correct, true for an economy Seat.
But if he wants to fly in J then using miles might be the correct choice, aside for getting ripped off for the 1-2hr flight.
Unless he finds a HC ticket from a major airline who's making a stopover in yul and then to nyc, which I'm not sure he will be able to find.