I have something similar-the Joovy Caboose. I used it at WDW about 2 weeks ago. I do like the drink holder on the model you're looking at! Mine does not have one, but does have netting on the back of the seat to store cups.
Here's what I found......I have a dd 15 mos (~22 lbs), and ds 4.5 years (~40-45 lbs). When both kids were in the stroller, it was harder to push (say 25 lbs empty stroller + 40 lbs ds+25 lbs dd= around 90 lbs to push). Not impossible, but going up hills and ramps especially at the end of the day was not fun. The other thing that drove me nuts was when people jumped in front of me or stopped. This thing was exactly easy to stop quickly or start up again with both kids on board. We stayed at CR so the monorail was a bonus. We didnt need to fold it up. However, riding the buses was not fun with this thing. It weighs around 25 lbs (and thats without the basket filled. I added a side bag to hold ponchos and a rain cover too). My dad carried dd on the bus while I dealt with the stroller. On mine, the wheels lock when folded up so you have to pick it up vs rolling it along. If the bus was crowded, it was not easy lugging this thing past people without banging into them. It also took up a lot more space in the aisle and aside of me.
Other than that, it was cheaper for us to buy vs rent for our stay. Both kids spent most of the time in it so it was handy. I did love going back to my Mac Quest when we got home. Soooo much easier. I did see many Joovys at WDW though. If I had to do it again, I might consider driving my own car to the non-monorail parks with that stroller.
alison