Whether or not you should get a stroller is a personal decision that only you can answer. Everyone tours differently, choose to parent differently, and every kid is different in what they can handle. For us, we went for 2 weeks in August and our 7 yo did not use a stroller or need one. We did have a single for our almost 2 yo but the 7 yo never rode (or even asked to). We spent 10+ hour days in the parks, but took in-park breaks as needed and it worked great for us.
Some things to consider if you do bring one:
- You'll need to fold it for the buses, and generally that will mean needing to take all of your stuff out of it for it to fold and carrying all those items on the bus.
- Be careful with the types of snacks you bring and how they are sealed as squirrels and other critters do like to forage, especially if food is left out or open.
- CMs can and often do move strollers around, so it may not be where you left it.
- There isn't always a central location in the parks for stroller parking so you may have to backtrack or go out of your way a bit to get it when you need it. Depending on the park and where you are when you need the stroller, it could work out, or it could add extra time and more walking which might be counterproductive. You might not have much warning that it's going to rain (or could start raining while you're in a show or something), and if the rain gear is back with the stroller, it might not be so helpful. Same with snacks, it may not be so convenient to backtrack to the stroller whenever someone wants a snack.
- August is known for raining, so always cover your stroller if you're planning on leaving it.
- Don't leave anything valuable in the stroller. The more stuff you leave and the longer you leave it for, the more attractive it may seem to potential thieves.
- Pay attention to height and weight limits for the strollers. A 7 yo may not fit comfortably in some of them and some may be tough to push if they aren't made to accommodate the weight of an older child.
Personally, I'd carry a small bag with snacks and ponchos or have everyone carry their own stuff in a small bag, take breaks as needed, and leave before the kids start to crash. Swimming at the resort after a day at the parks (especially in August) is a nice way to wind down if the kids aren't quite ready to crash when you get back and then you don't have to worry about dealing with a stroller, kids falling asleep on the bus, etc. Do whatever you think is best for your family, but I would personally skip the stroller with a 7 yo.
