Each year I organize an annual ski trip for a large group of college friends. Now that most are married, some have kids, etc. this is often the one time each year where we can all get together in the same place and have a good time... it's become an awesome weekend that we all look forward to and I am happy to put it together.
That being said, it's a huge pain in the ass to plan. I have to find a date that works for anywhere from 15-20 people. I have to find a house that can accommodate us depending on dates, availability, and final # of people (and not a ton of places comfortably sleep 20 adults, by the way.) I have to put down a deposit, which I just go out of pocket for since it gets returned after the trip and I'd rather not have to screw with refunding 15 people $50 or whatever. I have to chase people down to get them to commit, I have to chase them down to get them to pay. People drag their feet paying so I end up laying out cash for them and feeling like a jerk badgering them to send me their money.
We usually do a t-shirt, so I end up designing it (hard to come up with a new design every year!) and going out of pocket for it until folks pay me back for that, too. There usually ends up being a couple people who, at the last minute, either decide they suddenly do want to come or decide they actually can't come, so there's all kinds of rebalancing of the cost or stress about not having a place for everyone to sleep. This year we are doing a murder mystery dinner party one night, so I'm trying to shop around for a game to buy that suits the number of people we've got. Basically it's just a pain in my ass, but I'm *mostly* happy to do it since it means so much to everyone and we always have such a great time.
This year I'm drawing a harder line, though, to make things easier for myself... if you want to come, you MUST commit by X date, and you MUST pay by Y date. The cost will include lodging, the t-shirt, and the cost of the murder mystery game. I'm also doing a no refunds policy... if you pay and you end up dropping out at the last minute you're not getting refunded. I'm considering adding an additional $10 per person just to make sure I don't end up out of pocket when things are all said and done (which has happened in the past, either for the t-shirts or because people back out and need refunds and then I have to bill people $7 each to make up the difference and people don't pay, etc.) I also am just tempted to do it because honestly it's a commitment (and hassle) for me to plan it to begin with.
Has anyone else done something similar when planning events for large groups of people? I don't want to feel gross profiting off my friends, but I'm also not trying to end up $x out of pocket each year just because I have the misfortune of planning the whole thing. I'm thinking that if the cost per person ends up being $190, I'd just round up to $200, and if that means I end up with an extra $150 in my pocket then I just consider that my fee for spending months putting this shit together. Am I an asshole?