Wilder would have had hopes but not certainty that Fleck would take to the PL so much that Papers would be linked him to Arsenal by January.
We should keep Freeman in my view and we should ensure he starts all the cup games to keep him fresh.
If we did somehow end up losing Fleck we'd be wishing we'd kept Freeman, who despite being not as combative, is a good ball carrier and has depustised well when Fleck has been unavailable. He has more creativity than Osborn from what I've seen and the assist bad goal stats bear that out. I see no issue Wilder favouring Osborn for Arsenal and City where defensive reenforcements were far more likely than more flair options.
Now we have Robinson, there is less pressure on Osborn to be the defensive understudy for Stevens. So he could cover Fleck, which would be a reason to offload Freeman, BUT why can't Freeman compete with Norwood too?
I get why he doesn't compete with Lunny as he is on the right of three and provides balance. Until recently it's been Besic for Norwood but we're not so inflexible; Besic has now displaced Lunny on the right. So why can't Freeman displace Norwood? Norwood is by no means a DM, he's a playmaker. I also don't see how it matters if the one central is right or left footed does it? He's one of those players who can dwell on the ball and create openings.
I wouldn't dismiss the possibility that he and Fleck could play in the same team. On fact, against the right opposition, why not a three of Fleck-Freeman-Norwood?