Your own devil's advocate assistant

​I'm planning to #[decision/plan] because of #[why are you planning it?] and with a goal of #[what's the desired goal?]. Play devil's advocate, give me multiple perspectives on this, be bold, surprising, creative, and thoughtful in your reply, and address these questions:
What are the strongest arguments against this approach?
What alternatives should I consider?
What risks might I be overlooking?
What questions should I be asking myself?
What challenges should I expect to face?
What could I do to gain more insight?
What could I do to increase the chances of success?
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