Best silent auction item I ever saw: a best-selling writer would put you as a character in their new novel. If you were a librarian named Jane Eyre, for instance, she wrote a scene where her protagonist would have to go to the library for something and would interact with Librarian Jane Eyre.
I've heard of auctions like that. The only book I've read where the author did this had several characters named this way. Most were fairly minor, like your librarian example, but one was a recurring character who actually affected the plot. He was also an
odious toad of a man with no redeeming qualities whatsoever. Apparently the guy he was named after found that delightful, though, so no harm.
I only have one real raffle experience. A colleague and I had to go up to the local high school to try and drum up business for our library. When we saw the awesome HS library we understood why no one bothers to come to us, but we had to try. We had a table in the lunch area, and to draw people in we had a prize wheel. Turns out people really, really like to spin prize wheels.
Most of our prizes were dumb little tchotchkes, bookmarks and buttons and the like. The fake mustaches were very popular, we're definitely getting more of those for when we go back. We tried to be honest with the descriptions of the various prize quadrants - "Something you actually want," "Something you may want," "Something you probably don't want" and "Something you definitely don't want." The definitely don't want kids got a paperclip. We bought colored paperclips, though, so some of the kids actually liked them. The probably don't wants were the tchotchkes, the may wants were advance reader's copies of teen books, and the actually wants were gift cards to the local movie theater. We only had two of those, one for each lunch session. We intended them to be our big draw, but both of them were won within three minutes of the start of the lunch period. Feh.