If I had just ONE tip to give, this may not be IT, but it is still a good one.
We have been taking our double stroller to WDW for 11 years. Here's the scenario:
A. Dad pulls up to the curb at the airport, we unload luggage and carry-on stuff (camera bags, packpacks, etc.) into buggy (assume double stroller has front seat which lays down flat). Mom takes luggage to counter. (If you check luggage curbside, skip to step B). Dad parks car or volunteer family driver drives off.
B. Once luggage is checked, load carry on and small children into stroller, head for security. Unload from stoller onto conveyor belt - reload on the other side of x-ray. Continue to gate.
C. At gate, take stroller (still loaded) to the end of the jetway. Unload. Fold up. Leave at end of jetway for airline to load.
D. Once you disembarkin Orlando, stroller will be waiting for you on the jetway. Open it. Load it.
E. You can push this on "as is" to the monorail (from gate to concourse). Take elevator to luggage pickup. Pick up luggage and use stroller as a luggage rack.
F. Now, it would seem silly to bring your strolller solely to serve as a luggage rack, so here is how you continue to use it:
1. If you have young children, it will save you money (the cost of renting) at the parks. (Obvious one)
2. If your children are over 3, it will be more comfortable than a stroller you can rent. (Because you can lay the back of the front seat down and they have leg room)
3. The path is long from bus or parking lot to park (or resort, or whatever) - and you could really use a stroller before you have the opportunity to rent one in the park.
4. If your children are over 3, but under 80 pounds, they will be grateful for the opportunity to get a ride after walking a few miles. Trust me, they won't care what anyone else thinks.
5. It provides a great "cover" for a bag (say, a soft-sided, insulated bag) of snacks - especially when covered with rain ponchos.
6. It provides a place to store wet ponchos (under the seats) until you can get back to the room and hang them up.
I could go on - but there is enough here to spark you imagination. Suffice it to say that this strategy has worked so well for use that we have owned a series of 5 double strollers over the years....