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I think it could work.
Bobby for a bloke, Bobbie or (shudder) Bobbi for a female, who I'd expect to be Robyn rather than Robin. Why not? I don't think Robin (m) or Robyn (f) need nns, but the Bob names aren't a major conceptual leap.
I once worked with a Roberta, known as Robbie, and I was at school with a Roberta, known as Bert.
I once worked with a Roberta, known as Robbie, and I was at school with a Roberta, known as Bert.
Yes, I think it can work.