At what point do you guys think it's reasonable to begin asking for donations? I am still under 500 users but steadily growing and getting 100 to 200 posts a day. I particularly like Jeremy's idea of offering a special donations tag and lettting them choose their own title but I don't want to seem money hungry or appear to obligate anyone.
Also, since I am running an MP3 upload site I can commission a mod to set quota limits on uploads and maybe charge for anything above a certain amount, like some are doing with photos. Just tossing around ideas out loud here