I'm not against the idea of selling both, but I doubt we will as that would leave us needing to sign at least another two wide players and we have difficult getting any deals over the line at the best of times
In a choice between selling Gray or Iwobi, I'd sell Gray every single time. Gray contributes a worldie now and again, but otherwise he's hugely predictable and not particularly effective. Iwobi has his faults too, but he is one of the more creative players we have, so I could live with keeping him for now.