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Do I take another Signature token when I buy a second Work by the same Artist?

The rulebook's buy and sell steps place and return one Signature token per Work.

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Yes. Each Work you buy takes its own Signature token (unless it's the commissioned one), and you pay the Artist's current Fame. Both tokens move together as the Artist's Fame rises, and when you sell one Work its token returns, leaving the other for the Work you keep. An Artist has at most two unsold Works at a time.

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