In November, we took our 4 year old and our 4 month old. We rented a double stroller and also brought the Lillebaby for the 4 month old. He probably spent more time in the Lillebaby than the stroller (so I could wear him in line and on rides and such) and the 4 year old had plenty of "I'm too big for a stroller!" moments and wanted to walk (which we did not argue with- she recognized her own limits and always had the option to sit down and ride when she got tired, which she took when she needed it). Even still, the stroller was the best thing ever. I'll be sad when I no longer have a kid young enough to justify a stroller! Kids (and adults, let's be honest) need a lot of
stuff in a place like Disney- a diaper bag, snacks, souvenirs, just-in-case ponchos and sweaters and jackets, extra changes of clothes, water bottles, etc- and our stroller's primary function was not as Transporter of the Kids, but as Carrier of the
STUFF. We rented from a company which dropped it off at our resort rather than renting in-park, and although people complain about getting them on and off transportation, it really was not hard at all. All that stuff was put into designated bags when it was time to get on transportation, the baby was put in the carrier, and the stroller easily collapsed by tugging the strap with one hand. Mom, Dad, and 4-year-old each had a bag to hold on to on the bus / boat ride, and when we disembarked, everything got plopped on/under the stroller again. I'm dreading the day when we have to take a trip and carry the bags ourselves
(Yeah, I know older kids don't need diapers and wipes, but the rest of it is still a pretty good idea...)