I think this is a great idea. However, it will require a lot of planning and kicking people up the bum..
I recently attended a 25th Jubilee cadets thing. We had some cool stuff in store (Past vs Present serving members, shooting, confidence course, 5 course formal dinner, pre drinks registration night, brunch catch up etc). We paid up about four months in advanced I think, there were 40 people who paid from each side. Even after a deposit and all the lead up, only a dozen or so of us went?!
I'd suggest some cool stuff to entice people (not just the fun factor of meeting everyone) just like Jase has suggested. Then perhaps a big meal somewhere that is pre-booked, pre-paid. Ask for some money up front. If you choke last minute, tough titties.
Sounds ruthless but I am trying to be realistic. Many of the big great idea get togethers end up with drastically less numbers than imagined.
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