Good morning, I am heading to WDW during the last week of September with my wife and two daughters (ages will be almost 5 and 1 1/2). We rented a double stroller for the week from Orlando Stroller Rentals, but I am now wondering if I should get two singles instead. Our thought process is that if the 1 1/2 year old is melting down but the older child is still good to go it would be helpful for one person to leave the park but still have stroller if necessary for the older child. One of the cons would be that it could be hard to chase two kids while we have two strollers, but my in-laws are also going so we have two additional people to either push a stroller or walk with a child.
Could go either way. I’d lean toward a double stroller, because it does offer more overall flexibility. Two strollers will ALWAYS tie up two adults.
But if your double stroller is particularly unwieldy, I might question that. We’ve done the one double-stroller thing without much issue a few times at Disney.
Double stroller all the way. By the end of the day, you’ll have both kids sleeping in it on the way back to the room.
Also, when the CM’s move your stroller, you’ll only be searching for one when you exit the ride instead of two (put something easily identifiable on it, so it’ll stick out).
I faced this same dilemma last year. Our girls were almost 1 and 5, and we had 4 adults. We brought 2 strollers. It worked out ok since we had so many adults to take turns with the strollers. However, I don’t recall one time that we split up. When the little one got fussy I carried her with the ergo. My older daughter wanted to walk more than expected as well, so we were often pushing an empty stroller.
We took 2 single strollers but bought a set of clips that attach them together so one person can push both. It isn’t as convenient as pushing a double stroller, but gives you the flexibility to separate when needed.
I think the opposite, that the two strollers will offer much more flexibility. There are 4 adults here and the 5 year old won’t likely need the stroller the whole time. When I have friends with 2 kids I almost always recommend 2 single strollers. I would suggest am umbrella stroller for the 5 year old, when you are walking with purpose to make rope drop or at the very end of the night and she just needs a place to sit, etc. The rest of the day you can mostly strategically park it. You aren’t required to always have it with you. Then bring a more “full fledged” stroller for the younger daughter to nap in and have a more comfortable ride, and exactly like you said, be able to leave early for bedtime, etc. You also won’t have to worry about continuously navigating a double with only one kid in it.
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Actually, truth be told, I would go with option 3: A single stroller.
I don’t think a 5-year-old needs a stroller. I think a 4 year old MIGHT need one.
But that wasn’t given as an option. 
We’ve never needed a stroller for our children while at Disney or WDW after they turned 4.
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I second this suggestion. We took our City Mini GT for our 1 year old and used an umbrella stroller for the 4 year old. Both strollers fold super easily and fairly compactly. Our 4 year old would be in and out of the umbrella stroller, but because it was cheap, we didn’t think twice about leaving it for long periods of time at various stroller areas. It definitely was critical to have the second stroller though, because our 4 year old definitely would get tired of walking and would take short naps allowing us to keep going for longer periods of time without true breaks. I feel like a double stroller would be cumbersome to take on the bus and monorail and perhaps unwieldy in crowded/tight spaces.
Double stroller. Only one thing to push. One thing to park. You will rarely split up and need both strollers in use.
The empty seat can hold a backpack or shopping bag. Just get the one.
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We got the dbl stroller but watched people with 2 separate ones. Our method was DH dropped off kids with me as we started to get into line, he parked and then jogged over to us and it was seamless. Also creates a little clear path for us when walking 
Was easier for one of us to leave and get stuff and if we needed to move stroller while waiting we just moved one, instead of two .
We watched couples with two and I swear so many times they would get separated or start to drift in one direction and not be on the same brain wave all the time. DH noticed it first and then we started watching lots of times this happened.
Monorail - super easy, never folded it up.
Bus - have to fold regardless so dH stood with it in the back while i had kids sit with me. super easy. and we aren’t a dbl stroller family since our kids are 4 and 8. 8 yr old only does stroller at wdw
Buy a stand n sit stroller off of craigslist for $40, check it at the airport and leave it somewhere on departure day. Those doubles suck navigating through crowds. Cheaper than a stroller rental too.
We did 2 strollers the 1st time, the rented a city mini double the 2nd and third time. The double was WAY better. Yes, a little big to get on the bus, but it folded by grabbing two handles in the seat- super easy for DH. The city mini double fits through all doors and monorail. The rental also came with a rain cover, great during downpours while we were inside.
^ This
We did a double for a 3 and almost-6 year old in January and were so happy to have it. I have seen two umbrella strollers that could clip together but I imagine they can be harder to steer??? (Though if they push easily, that seems the perfect solution!) We were glad to have a stroller with 5 year old - we criss-crossed the parks regularly and we got everywhere SO MUCH FASTER with them in the stroller! Plus, they needed some down time during the day. I’ve also seen people rent one stroller and then rent a park stroller for older child if needed. Would you bring an ergo or carrier? If so, then one stroller may work for you! If you need to split up, 1.5 yo can go in ergo and 5 year old keeps stroller. The stroller rental places have such nice strollers, roll so easily, so easy to handle and fold, can store a lot of junk on the bottom - I will be a little sad (but happy for the freedom of not parking a stroller!) when we have to carry our crap with us instead of shoving it in a stroller! (Tip, though - since you have to fold the stroller, make sure you keep everything in there in a backpack or a bag so it’s quick to grab out. We kept a small backpack with valuables and another drawstring bag (for sweatshirts, jackets, stuff we didn’t care a lot about and left in the stroller at all times. You’d need a diaper bag, too, but I’d be willing to take my chances leaving that in the stroller as long as it’s not expensive.
I’d grab the backpack out when we left the stroller and even left it in sometimes. That’s taking a chance but I’m not hauling EVERYTHING around and we can afford to replace it if needed. Just don’t shove loose things in the bottom because you’ll be frantic to get them out when it’s time to fold up! The dollar store sells little drawstring bags with one zipper pocket and we’d bring an extra in case we picked stuff up along the way.)
Throwing out an alternative. Rent a double & buy a cheap single umbrella you can stash in the basket or leave in the hotel room in case you need it.
My kids are 1 & 3, so no advice on when to post the stroller