Waiting for our gate checked stroller is the most stressful part of traveling with my four year old. I can't imagine doing it with more than one.
I don't know how Delta is with gate checking, but American is all over the place, and I've almost missed connections of this length because American took so long to bring out the gate checked stroller. There's little worse than knowing your connection is leaving soon while you try to manage a toddler in a jetway full of people trying to get off the aircraft.