I would never send more than 2 items/pictures to be signed.
I do usually send two items (such as a DVD cover/inlay and a favourite picture), or say I write to a musician and I've seen them live then I send two pictures that I've taken at their gig.
I also include in my letter that I have sent two photos and would be grateful if they would sign one and add "or even both of them"... So hopefully they realise that I'm not a dealer, just a fan that would be happy with just one signature.
# of items to send
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