1 kid = maybe doable and worth risking, but with 5 kids, the likelihood increases that something somewhere is going to go off the rails. I'd do it only if there was absolutely no other option.

I get what the OP is saying about not wanting to sit around a terminal for hours with a bored kids, but he/she definitely needs a buffer of some kind... 1.5 to 2 hours would be the ideal. Should be plenty of time for everyone to use the washrooms, eat, move around a bit, etc., but if there is a problem like a flight delay on the inbound, at least there is still time to dash over to the connection without too much stress or panic.