My 8 year old will still sit in the stroller at WDW if there's an open spot, so yeah... it's just tough on everyone! I agree that your scenario sounds difficult, but definitely not impossible. Two years ago we took a bus back to our resort--it was DH, our 3 kids, and me. We had a double stroller. All 3 kids were asleep, and the bus driver was very patient while DH quickly dropped the stroller outside the bus and came back for one kid while I woke up the oldest and carried the youngest off the bus. If we'd had two strollers, he would've done the same thing. Something else we've done if the bus is down to standing room only is step aside to let other people on ahead of us. If we have 3 sleepy kids, we have to be sitting down, so sometimes it's worth a little bit of extra wait time.