Stroller as a wheelchair and Disney stroller rental?

Honestly -- for a 5-yr-old I'd just spring for a cheap umbrella stroller and use that. Assuming it will meet your son's needs. They can be picked up for as cheap as $20-$35 for a no-frills simple umbrella stroller. Most indicate max weight at 40-45lbs, and honestly it isn't going to break if the child is just a few pounds heavier. Easily folds and carries onto transportation, or fold it up and leave it in the corner of your resort room if not needed.
https://www.shopdisney.com/mickey-mouse-umbrella-stroller-884392606824.html
^^ You can get this exact stroller (Or the Minnie one) in the parks at the stroller rental locations for $40 … basically the same as 3 days of pre-paid rental.

They had a ton of them at most of the parks. The only place I didn’t see tons was at DHS, but its possible they just weren’t visible from where I was sitting.
 















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