The immediate goal of this document is to lay out how funding for my dating site might work. These ideas have been rolling around in my head for years, though, so I'll try to make this more general. The ideas are largely in response to National Public Radio (affiliates') semiannual fundraising events and Wikipedia taking up 1/3 of the screen with "appeals."
Note that I'm in no position to ask for money until we've had our first few good dates. After that, as an example, I might ask for the hosting fees to be donated. Assume we keep these fees in the $15 / month range. I'll start a time - money clock for $15 in the next 30 days. The clock starts at $15 and, if there are no donations, works down to zero, pro-rated over 30 days. Donations add to the amount.
As the clock reaches $0 and then starts into the negative, I and / or my inner circle prepare to shut down the site. Hopefully the code is already on SourceForge. If not, put it there. Inform users that they need to save anything they want to, write any last messages, etc. Give them a time that the plug will be pulled. See if anyone wants to adopt the site. If so, we have to give the users an opt-in option to move, otherwise they and their data will be deleted.
This clock would appear on one or more screens of the site. It should not become intrusive and should not be on every page, and/or should not be shown particularly often--often enough that a person sees it every week or some such. It might get occasional mention in any forums that develop around the site, but no harping! There might, of course, be forums devoted exclusively to debating and watching the clock.
And that's that. No constant appeals, no two-week-long fund drives, etc. Don't tell your users how great you are and bemoan what the world would be like without you. The radio variant would be to describe the creation of the clock and then occasionally mention the number and refer listeners to the web site for further explantion. A separate clock could run for different shows.
The amount, timestamp, and sequence number (donation 1, 2, 3, ...) of any donations will be posted to the site. Donors will also get so much space for identifying themselves and perhaps even advertising--this will be the only advertising allowed on the site. Perhaps bigger space for bigger amounts, in which case there should also be a list that gives the same amount of space to all donors.
On a related note, there could be a conditional pledge, and/or specific-purpose donations. For public radio, this would mean allocating one's donations amongst different shows. A side project of the dating project could be to create some open source code that assists creation and accounting of these various "buckets" / sub-accounts.
For this site, a conditional pledge would be, "How much would you give if we implemented such-and-such feature?" Or "We'll implement this feature if we get pledges (not donations yet) of $n." Then we can work some system of partial donations versus partial implentation.
Organizing the site into a 501-c (3) non-profit, with tax deductable donations, is possible. The mission statement would be something to the effect of "To improve the world through love and contributing to the open source code base." Beyond that, I'd have some very specific clauses I'd want before I took the site out of my name, but that's beyond the scope of this document.