I am in an identical situation, dd who turns 4 on september and we too had a Chicco Caddy (which I loved when she was less than 2.5).
Since we had a trip to NYC back in june, I decided, after seeing all the Maclarens, that the Quest was the stroller for us. We bought the pink albee baby exclusive and can´t be happier with it.
What sold me the Quest over the Volo is that the seat seems more comfy because it can be extended. I know I will never extend if with my dd because of her age, but it somehow seems softer or kinder to the back of her legs with the fold than if it had an edge there. I don´t think I am explaining it well (English is not my first language).
And also because she is older she doesn´t fall asleep as easy as before, so it helps a little to have her reclined.
The basket holds a lot more than you would ever think, though it won´t hold a huge diaper bag, but it will hold the contents if not in the bag.
She can hop in by herself, has a good harness system, and her feet can rest on the foot band (not like in her Combi stroller where the foot rest was too high, so her feet would dangle and would stop the wheels) and the seat is really deep, so she looks very comfortable in it.
I am editing because I forgot to add that it is really easy to push with my dd (38 lbs) sitting in it. I pushed her all through Manhattan and will be using for our upcoming trip to WDW in september.
We hardly ever used the combi because we bought it when my dd hit 33 lbs and it was soooo hard to push with her in it (and also the other things I mentioned). It was so bad that last september on our trip we decided to leave the stroller at home and
rent a stroller from
www.abbf.com