Personally, I wouldn't. I did it once before and it wasn't very much fun, to be honest. I do love Chef Mickey's and I don't have much problem going from one thing to another, but it did feel like a bit of a rush and was not fun for my kids.
How old are your kids? Older kids might be more up for the "rush" than younger ones.
I wouldn't worry about delays -- if you don't get in on time, you don't go, not that big of a deal, but even if you land on time and get to your hotel by 6:30 to begin checking in and getting in to your room, how quickly will you wnat ot turn around and rush out to get to dinner. I thinkyou would need an hour to make sure you get checked in, get your luggage to your room, settle in for a few minutes, use the bathroom, "freshen up" a bit....and then get back on a bus at 7:30 for an 8:00 ps (will you be hungry before that after travelling all day? How long was your flight? What time did you leave in the am?)
And dinner at 8:00 - not back to the room until about 9:30, then need to unwind and fall asleep to get up at what time for the parks??
Anyhow, I always thought the idea sounded great, but when we did it, it was too much -- and our flight landed before 4 pm.
Just my thoughts after having been there....It definitely can be done, but not sure it's all it's cracked up to be. Maybe if you land before 2:00, but when arriving on the later side, it's kind of a rush.
Actually, I would consider it if it was a pretty short flight, my kids were older, and I was staying at the Contemporary -- then it would be less of a rush.
Hope that helps!