[William]

Well, I guess it depends on the result of his evaluation of the Shedite's redemption chances.

He's not going to let the Shedite ruin any humans' lives. Even if the Shedite is making an honorable effort to avoid doing so, I would imagine this would be very challenging for all the reasons discussed in this thread. But if the Shedite is making an honorable effort not to damn humans, it has jumped one of the most serious hurdles to Redemption -- it's thinking about someone other than itself. That suggests that it would have as good a chance as any demon of surviving a Redemption attempt.

A long period of coaching would be putting a lot of humans at risk from the Shedite's bad habits. Much easier, yes, to approach the Shedite openly and offer a Redemption attempt via one's Superior. Coaching away any bad habits can come afterward, when the Shedite is a Kyriotate.

If the Shedite is not making an honorable effort to avoid damning humans, of course, then it's just a Renegade Shedite with little chance of surviving a Redemption attempt and should be sent to Limbo or somehow captured.