Essentially, that's what we've been doing in the past two years. Two fundraisers every year. (In the first two years, while we could, we paid everything from our own pockets). I know it must be annoying or tiring, but that's the best idea we have for now. We've tried countless potential advertisers after our first advertiser (Astroloquiz), but most won't even respond. We will keep contacting them - ones that offer some relevant service to teachers - but even if we succeed, it's still pocket money to keep a busy webportal like ours running.
I know what you feel, because I feel the same thing, and I wish we didn't have to do fundraisers twice a year. (Wikipedia's model is very elegant with a once-a-year fundraiser, but virtually the whole world is a user of Wikipedia, and they are also eligible for grants, so this is what affords them this kind of luxury.) Yes, it's a fine line we're balancing on, but I'd like to believe that our members will vote with their spare change to keep the site going, like they had done so before.
As for the future, we'd like to have a lot more security, too. We have some ideas as to how to keep the materials freely accessible, since that's our core mission, and have some other revenue stream other than donations. However, before we can come up with anything, we have to stabilize our finances, the new staff and the new work processes.
Thanks for caring and supporting us!
To those who feel they would miss iSLCollective, but have been hesitant so far to join our efforts: Only 17 days to go, and 74% of our budget still needed!