Reading all the ideas - both the one-year-long raffle idea strikes me as interesting, as does the 2x a year "push" raffle.
What I think I prefer about the 2x a year approach is that it's focused. People experience fundraising fatigue - any person in the US who is old enough to remember how PBS (Public Broadcasting Service, our television channel that was run non-profit) seemed to be running their fundraising drives nearly all the time. I worry that trying to do something that is 'alive' literally every day of a calendar year will run the risk of becoming annoying, like a constant pressure to give.
A focused push - something that lasts for a month - does end up missing an appeal to individuals who happen to not be around during that month. However, it isn't a difficult period of time to keep the buzz up for. I felt very fortunate that this year, the novelty of the first raffle and the low-ish target goal meant I didn't have to do a ton of promotion for it. We were pretty low-staffed at the time. But I don't expect that will be the same on a second raffle; I expect that (given the increased annual goal) the bar will be set a little higher, and people are going to need more motivation to give - just, the thing has to have more visibility overall.
And then it gets to go quiet, and just bubble along under its own steam until the next push period comes around.
Two years ago, when donations were especially slow,
@Nicolette put out a call to action that resulted in a highly motivated, 30-day fundraising push. It was great for the community and raised a lot of money in a short period of time. That was a one-time kind of thing, it can't be repeated; but, I remember how effective it was being partially due to about 15 members being really willing to talk it up in chat, with new people, running little mini-contests in Social, a bunch of us changed our avatars to spread the word about it - the communication and involvement was really good on that one. If we do decide to go with the one-month push structure again (whether repeated 2, 3, or 4 times), I would like to be more proactive about recruiting a team to engage with it, as described above. It will increase our chances of getting more new dollars, and it will be more like the membership talking to the membership, less like admins talking to the membership. That's usually helpful when fundraising.
That structure wouldn't work in a one-year raffle; that would need to be promoted regularly by staff. And that's also possible. I suspect that even if we structured it as a one-year arc, it would still need one push month in order to be truly successful.
That's all just based on my own fundraising experience, both here and elsewhere.
