My opinion is different than most, but here goes...
Those high end strollers are a waste of money. $500 or $600 for a stroller? OMG, no. We used strollers for our kids at WDW, including our twins, until they were 8 or 9. We had a double stroller that we bought from Wal-Mart or Costco or Target, frankly I forget which one specifically. It wasn't the cheapest, flimsy umbrella stroller, but it was around $80. Something similar in concept to this...
https://www.walmart.com/ip/Kolcraft-Cloud-Double-Umbrella-Stroller-Scarlett-Red/44390754
It worked great for years. Handles weren't too short, had enough shade...the one we had also had storage underneath. We loved it. The last trip we used a stroller for our twins, we had sold that double stroller. So we went on Craigslist (actually near Disney) and bought a used one just like this...
https://www.walmart.com/ip/Baby-Trend-Double-Jogger-Millennium/14895501
We paid $50 or $60 for it, I forget. It was bigger and bulkier than the smaller one, but the big wheels made it ridiculously easy to push our twins...who weighed about 80lbs each then. It worked fantastic. Right before we left, I put it back on Craigslist and sold it to another vacationing family for $40.
I'm not suggesting you need to go to all the lengths on Craigslist that I did...though it was actually quite easy...but my point is I think it's a waste to spend $500 on a stroller. There are options that will function exactly the same for $150 or less...way less.