This post reminds me nearly exactly of the recent post where a couple flew a discount airline from Bilbao to BCN??. The flight was late, and he missed the DL award flight in J to the USA, and DL wouldn't do anything, and ended up paying $5600?? to buy new J tickets - and blamed DL for not helping him.
IMO, if you have checked bags - FUGGEDABOUDIT! Without checked bags, you hava shot a making it.
Again, as mentioned above: You'll hafto clear Canadian immigration and customs. Deal with bags, if any. Get to DL - check bags if any. Clear US immigration and customs, then security. Possible long walk to a gate.
When I flew the NW Bucharest deal out of YYZ, I think I allowed most of the day (6 hours?) between my award ticket and my YYZ/AMS/OTP legs. I
DO REMEMBER that, when I told the Canadian immigration officer that I was going onto Europe, they sent me to a secondary immigration screening area for more thorough questioning!!!