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If I have a skill that lets me attempt skill check X in place of skill check Y (for instance Orator: http://www.d20pfsrd.com/feats/general-feats/orator), which skill focus/magic item/etc would I need to gain bonuses?
Use whatever bonuses apply to the replacement checks.
See this FAQ. It gives an example of a circlet of persuasion.
Ahh, I missed that. Thanks!