We have traveled to WDW many times with a stroller. After the first time exiting a ride and not seeing our stroller where we left it we learned it is a "just relax and survey the parking area until we find it" because the CM's have a heck of a job keeping some areas clear enough for people to walk.
Funny side story, our daughter always took her doll, Sarah, on vacation. Sarah had a very nice wardrobe because grandma found out that preemie clothes at target were cheaper than doll clothes. Couple that with the fact that when in the parks when our daughter was not in the stroller she would put Sarah (the doll) in the stroller and position her so she looked like a real child ( she would partially cover her face with the blanket and leave her feet showing so you could see the real child clothing. We came out of the store in frontier land after trading pins and proceeded to the stroller parking area next bear jamboree and we were met by a very angry cast member (old enough to be a grandmother herself) and were admonished for leaving our baby in the stroller. WE ARE NOT BABYSITTERS, YOU CANNOT LEAVE YOUR CHILD IN THE STROLLER FOR US TO WATCH!!!!! At which point we removed the blanket and informed her it is a baby doll. She turned and left without a word.