We always worked from the assumption that the principal had informatin none of the rest of us had, or needed to have. We give the principal a discretionary fund, and allow him to handle it from there. I would be tempted to treat the vendor freebies and such the exact same way.
I would never condone rigging a raffle. If you present the event as a random drawing, then that is what it needs to be. Otherwise you run the risk of creating an atmosphere of distrust. Some kids may not need the prize, but they sure are excited if they win the prize -- don't rig the outcome.
One of the things we started doing last year, with mixed success, was offering pre-sale tickets to all events. We have a couple of dinner social events that never offered pre-sale before. We pitched the pre-sale to the school as an opportunity to jump the line, bypassing the cash box and going straight to the service queue. What we didn't advertise was that it also allowed the principal to use discretionary funds to assist families that might not have otherwise been able to attend.
How many people did he distribute tickets to? I have no idea. I sure hope he was able to help some.
In promoting our festival each year, or the Holiday Shoppe, we ask Trivia questions over the morning announcements for a whole week before the event. Students send their responses to a jar in the Media Center and we "choose" winners who get free tickets to the festival or a gift certificate for the Holiday Shoppe. We had 35 kids on free or assisted lunch last year, so we gave away 45 prizes. The teachers distributed the prizes within the class or we gave them to the principal who put names to them based on her lunch program list and gave them to the teachers.
One parent whose daughter regularly "wins" was very offended when she was "given" something else by the school. She was on the fundraising committee and hasn't caught on. Also, some of the kid-in-need come in with lots of money to spend, even with their free certificate. You never know. Just believe you are getting the helping hand to someone who does appreciate it.
Have you tried talking to the school Counselor about this? They would be the one that I would bring the matter up with, ask how they think it should be handled. When we do things for children we never ask the teachers to identify them. You mostly can see who they are, but might be surprised by some that are really in need but don't look or act it. One way we did this was at Christmas last year we gave gifts to those that would not have one to exchange. We did this through the teachers. We did not advertise it to the parents as some would have unfortunately taken advantage. We only asked the teachers to tell us how many gifts they needed, if they were for a boy or girl and if we needed to find dolls of a specific race. Then we delivered the items to the teachers early, without the children there. The teachers took it from there. This way the children's pride was protected and they weren't made to feel bad. As for them applying for this assistance, I agree with you they are for the most part the proudest. Our school helps parents get Christmas gifts and other items, but again it's through the teachers/counselor with them being the only ones that know who are getting the items. At Pre-K open house there was a lady there that was in charge of Peachcare (this is Insurance for children) no one came to her for information. Because, it was in a group and they were to proud. Some did get information later, on their own. Maybe you could divide the items up among the teachers. Let them play games or have some kind of contest and use these as rewards. Then they could make sure that the ones needing the items would get them. Without so many knowing. I would talk it over with your counselor. If they are anything like ours they are very helpful, caring and can come up with inventive ideas. Good Luck!!!
Here's the situation - our new school is drawing from a very diverse population - from low income/HUD housing to million plus households. I know that the house you live in doesn't necessarily mean you are rich, but . . . . . as a PTO we have an opportunity or two that costs us nothing to give away certain things. School supplies that are "extras" and the rep tells us to keep, as well as play money we are getting from our holiday shop vendor. I think that we could have a "raffle" but ask the teachers to identify the students who might be most in need or otherwise unable to participate. Others on the board think that we are playing with fire in so doing. It has been suggested that families could "apply" for this type of assistance, but my experience says that those most in need are also the most proud (perhaps there is a lesson to be learned from that) and won't apply, thus not giving these things to those who are most in need. If anyone has any experience with this type of situation I'd appreciate hearing from you. Thanks for listening and I love this place!