our son will be turning 5 when we go to Disney. I am wondering if I should bring our umbrella stroller for him. He just turned 4 now and he is 43.5 inches so he is not a small toddler just tall.... what is everyone else thoughts and experiences on this....
NOT. They're just too much trouble to deal with. If you decide you want one, just rent it from Disney in the parks when you get there. Cost a little more, but the convenience is well, well worth it.
Bring, but make sure it has a large canopy! The Florida heat is bad, and we are right next to the equator which means the sun shines almost directly on us. My husband once got sunburn just from walking from the car parking lot into our local mall! It gets really bad for people during overcast days - they think that they can't get sunburn - but you get it even worse there!
I see lots of little kids in strollers that have little to no canopies being miserable and burnt to a crisp. So be careful, but do bring a stroller - you will be grateful you did. Besides, it's either bring your own or end up paying Disney $$ to rent one, right?

What we did when my dd was 5 was not bring it and rent one in the parks if she needed it.
We did a 7 day trip with midday breaks and she never asked for a stroller. Not once. We also had two days before and after our Disney vacation visiting family in Orlando. Still no stroller.
We were thoroughly prepared to rent in the parks if needed. Thankfully we didn't and she did well. We also went completely bagless that trip. It was awesome.
Every child is different and you know what's best for your child
I think it just seems like it right now! It's freaking hot and the sun here is evil - if you get a stroller, get one with a good extendable canopy. And be prepared to sunscreen up those little toes, legs and even the arms and fingers. 