I have a few different answers from a few different perspectives. Let me toss those out first:
On Fun
We definitely need more of it. We need vents for the steam we generate here. Hard stop.
When meta originally launched, shenanigans were permitted provided that they were clever enough, and that they didn't turn the place into a cheeseburger network. It was a different time; Jeff's job was to care about and read every single post and every single comment as well as write most of the code, handle the business end of things, make dad jokes on Twitter and occasionally answer programming questions. So, well, fun didn't scale.
When the first round of VC funding was eminent fun got downright scarce. I'm only pointing out the correlation because a little fun isn't really as big of a problem for the reasons it was originally discouraged. I do worry that it could overtake the site a bit if we just opened the flood gates completely, but doing stuff like finally coding a polling system for meta sites (similar to the one Twitter does with some additional gates around it) was something I was just talking to David about not long ago.
I think we need a place to let people be more human, and what you describe does that. We need CGF (Community Generated Fun).
On Expenses
Fun can't be at the expense of anyone else. That means it has to be great for whoever or whatever it's about. It can't be a way to lay blame or criticism on someone or something they did couched in a giveaway unless we're really careful and anyone involved is totally on-board. You can make fun of me all you want, but I can't volunteer anyone else or risk a bad light being shone on them for the enjoyment of others.
It also means you've gotta be creative and put achieving whatever the goal might be in the reach of anyone that wants to participate and is able to cross the very low threshold for participating here. We learned really quickly that we have to build a toggle to disable the auto-protect feature due to the number of responses, for instance. That's probably going to get enabled on posts where the author was an employee at the time it was written (still working that out).
Anyway, expenses here aren't monetary. They're the emotional cost of exclusion or embarrassment. It has to be done carefully, and it has to be a thing where people generally feel wanted and encouraged.
On Fulfillment
Since it's under our brand, we've gotta be certain people get their stuff. In fact, I was so bad at getting stuff sent to people on time that we ended up making a whole new process around that with multiple people working on it and lots of accountability.
We'd need some assurance that whatever it was, it'd be sent out. And since there are weird laws about contests and political sanctions and shipping logistics to certain parts of the world, as well as the need to convey personally-identifiable information for fulfillment needs (if it's on our site, our terms and privacy policy have to apply), it leads me to my final answer:
We're interested in exploring this, but coordinate with us before starting.
Shoot an email to [email protected]
and it'll work its way through the community team where we can help. We might not be able to do it right away, we might need to make some changes to the idea, but:
We'll seriously consider it with the intent of finding a way to make it work, if at all possible (the opposite of looking for reasons why it wouldn't)
We'll make sure everyone knows to thank you for it when it launches (we call this giving credit and it's a double-edged sword)
We'll make sure we do it in a way where we don't have to share private information in order for fulfillment to happen.
But, please have a concrete idea, or as close to one as you can get. What's the sweat equity needed? Can anyone easily do that? Are you sure you understand what anyone means? What's the reward, beyond the bragging rights of participating? What can we offer people that don't win the main thing?
If you do that, we'll see if we can match up with some goodies of our own and see if we can get behind it with you. But, we're right in the middle of overhauling our swag vendor and process (for the better), so it might be a month or two before we're ready to go full swing and try stuff.
I really like the idea of the community owning most of the fun this coming holiday season. So .. let's talk about it. And maybe we can work up to something where we can more clearly and simply articulate the rules and framework and be less involved (that would be really neat). But for now, we're game if you are!