I find it so interesting to read threads like this where opinions are at completely opposite ends. We have twins that will be 5 and we still take our double jogger to WDW and absolute LOVE it. Our girls love to pack up our jogger each night in the hotel room with their light-up toys and stuffed animals, light sweaters, etc. Then we head to park with late hours and the girls go, go, go until they get really worn out and they cuddle up in the jogger and fall asleep for the night. We love this! We recline the seats and make it really comfortable for them. We adults then grab a snack and enjoy some quiet time together while the kids sleep, then we take our time getting back to our hotel without having to wake the girls until we transfer them to bed. Now, having said that, I don't know how this will work at POR given that a bus will have to be taken back to the resort. I see that is where you're staying and we'll also be there in April splitting a trip between POR and WL. This is all new to us. We'll have to wake the kids up to load the bus. In any event, when you arrive back at POR, you can transfer the child back to the comfortable stroller and then go to the food court for a drink re-fill or late-night snack. It's great to have a stroller in Disney for times like this. It makes for such a relaxing trip when the kids have a place to rest. Otherwise, I think we'd be rushing back to our hotel room to get the kids to bed.
This is just what works for us, and it works very well! We have always had very relaxing trips and we feel it's because we've always taken a comfortable stroller/jogger from home.