Hi, all,
Jumping in here...
I was head chaperone/trip coordinator for my sons' WDW trips with their marching band, and after they graduated, I just couldn't give it all up (if you do it, you understand!). So now I am one of those group escorts. I work for a travel company and escort bands and choirs on trips of all kinds. Lots of Disney, plus band competition trips (mostly BOA), NYC, etc. So I am essentially getting paid to do what I did for free for ten years! It's a tough job...
I LOVE taking groups to Disney. Partly because I am so familiar with it that I can offer lots of helpful advice, but also, as several PPs have said, because it is so heartwarming to see kids enjoying one of my favorite places. For my own kids and those I have escorted, it was/is always surprising to them just how much of a rush it is to have literally THOUSANDS of people along the parade route cheering for them.
I believe the OP said they have a guide from the travel company who set up the trip, is that right? If that is the case, there are many things the director/chaperones do not need to worry about. One of the main ones is photocopying/keeping track of ticket numbers. At least with our company, I always have with me a binder with all the information I could possibly need, including phone numbers, confirmation numbers, and most importantly, a list of everyone on the trip and his or her ticket number. With large groups especially, there are ALWAYS a couple each day who lose their tickets, or forget them at the hotel, or whatever. The procedure is that I take those students to guest services, show MY ticket (so they know the "batch"), and tell them the number of the ticket that needs to be replaced. They void the old ticket and assign a new one. Only takes a few minutes. Our company also writes individual names on each ticket, so that if one is found on a bus seat or the hotel lobby or wherever, they immediately know who it belongs to. (Not to mention when four kids in a hotel room can't agree on who actually lost a ticket...)
None of the groups I have taken to WDW have collected the tickets after entering the park. To me, that is a cumbersome step and takes away the opportunity for fastpasses, one of the best features in the parks. For the PP who mentioned having the chaperones get FPs for everyone...wow, what nice chaperones you have! I guess it's like the Brazilian tour guides. I hope your group was not too big!
Several of the groups I have traveled with have done what one PP suggested, having chaperones at certain spots (they rotated shifts), so students could find them if needed, for medications or other issues. In general, meeting up during the day just to check in (as opposed to for a scheduled activity) is MUCH more trouble than it is worth. That takes a huge chunk out of touring time, which is already much less than a typical WDW trip because of the scheduled performances and other activities. My oldest son's trip was Christmas week 2000, and not only did none of the kids have cell phones, most of the chaperones did not, either! To me cell phones have totally changed the nature of such trips. And we have never had a problem with spotty cell service in the parks.
The meals can be set up a few different ways. Sometimes our groups get one credit-card type dining card for the whole trip. These are great and convenient (can only be used to purchase food and drink), but unlike park tickets, they CANNOT be replaced if lost. So if a kid accidentally throws his out with his trash, he is out of luck for the rest of the trip. Talk about a lesson in responsibility! They other option is youth program meal tickets. These entitle each holder to a combo meal, a drink, and a dessert. I tell kids that is a lot of food, so they might consider splitting one with a friend, then getting another one to split later that day. Admittedly, that advice works better with teenage girls, since teenage BOYS can generally eat anything you put in front of them...
Find out what your travel company has organized for meals and go from there. And use your guide. He or she has most likely been to WDW many times with groups and can be a valuable source of advice and info.
Enjoy your trip, I know your kids will! I am actually escorting a band from Louisiana next week for the Disney Honors program.
Let me know if you have any other questions!