A raffle, as you found, Illaria, might not be the best way to go. In the first case you mentioned, not everyone in the raffle is interested in a portrait. At least with auctions, presumably everyone who signs the bid sheet is interested (though some don't follow up.)
A way to prevent the second scenario from happening would be to specify that it is for "new clients only".
My auction experiences have been mixed. Of the 10 or so auctions that I have participated in about half have been worthwhile. The worst one resulted in a damaged frame, having the sample set up in a very out of the way corner, being in the silent auction as opposed to the live auction as I was promised, and no bids.
The best auction experience I had led to one of my very best clients who has since gone on to commission five three-quarter length oil portraits, and also led to a contact with an art school where I teach an annual workshop.
All in all, I would still highly recommend participating in auctions for artists getting started with their careers. It gives you exposure (if you choose the right auctions), experience working with real clients, and portfolio samples -- and often, you do get income from many of them.
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