I started bringing my own stroller after my first trip with my dd (she was 13 months at the time, will be 5 on the next trip in Dec - and in her stroller!) and I learned:
1. It is a really, really, really long walk from security at Chicago's Midway airport to the gate. Why do Southwest and ATA consistently put the MCO flights at the very end of the terminal?!
2. I learned on later trips that it is a really, really, long walk from security to the gates at the Indianapolis airport.
3. The walk from the bus stop to the hotel room after
MVMCP is the longest walk of your life.
4. I love the Disney strollers for all of the reasons mentioned above, but they really aren't comfortable for older kids, IMHO.
5. The buses are going to be too crowded with or without my stroller.
I recently purchased a Kidco Lifestyle stroller (got a great deal on "last year's" model) because it is still fairly compact, it has a 50 lb. weight limit, and the handles extend so I don't have to hunch over to push.
I strongly suggest bringing a stroller organizer with your stroller or to use with the Disney strollers. I got mine for about $10 at
Walmart. It packs easily and we store everything in it. It is clear plastic (the security folks love it) and it has a bunch of separate pockets. I used it instead of a diaper bag when dd was younger. Now we use it for sunscreen, film, water bottles, etc. I don't put anything valuable in it, but I have never had a problem with theft and it helps our stroller to stand out in a crowd.