Here’s a story from 2015..
My kid was 5, we are out doing activities twice per week- ie amusement park, trampoline park, museum, city park, etc..and he was in sports.
I didn’t even think about a stroller, by that age I had already given all of ours away.
And then...one of my friends told me I should use one.
What?! I laughed it off.
After several friends/family said the same, I decided to rent one at the parks.
I’m so glad that I did!!!! Heat index was over 102 every day of our trip, we were staying up until 12am or later, waking up at 6 or 7am.
I suggest reserving a multi day rental at the parks.
Here’s what we did-
Pick up stroller when arrive at park..
Parked stroller in fantasyland, walked fantasyland and Tomorrowland.. then went to collect stroller to run and catch our next FP..
Do the same for Frontierland and Adventureland.. then collect stroller and run to our Dining reservation. Rinse and repeat.
It was nice to have when we had to hurry and especially at night for Wishes..but most of the day we just left it parked. When we left we just dropped it back off.
If you use the train at MK then you just leave it at one station, collect a stroller where you get off.
So much easier than dealing with a stroller at your resort and on transportation.