If you think of him as Almiron, another quality and tiny South American winger who isn't a big goalscorer (until this year) finally doing it at 28 years old, it's not crazy that Pellistri, who is visibly quality (nimble, smart, aggressive, dribbling and first touch with both feet are good) but has a genuinely non-existent scoring rate and is 21, might need 2-3 years of loans.
He just doesn't seem to want to do it, as does anyone who doesn't join Chelsea or City really, which I imagine means they pay those players more?
Ideally we'd re-sign him to a longer deal and loan him somewhere for 18 months in January, with recall options in place, commit to bringing back Amad in the summer. But those guys are #5 and 6 choice for 2 spots out wide here at the moment, so unless Sancho leaves, I think Pellistri will just get a move from some team desperate for a RW.
He might start for Southampton or Leicester. Those teams have nothing out right, and while Southampton probably wants to start Edozie out right after bringing in Orsic to play LW since he's their own player, they have to be mostly focused on staying up at this point.