First rule of holes is applicable here. When in one, stop digging.
First, Roscoe wasn't a wing. He was a big who played the first few minutes of each half as a wing his freshman year because that's what it took to get him to willingly play most of the game as a 4. His second year, when he said he only wanted to play the wing, he barely played.
Second, when he played wing, he had Kemba Walker, Jeremy Lamb and Shabazz Napier as his guards. We didn't need points or shooting from a 3 in that lineup. You want to compare any of our current guards to any of them?
Third, Akok Akok is not Roscoe Smith. Even if he becomes as good a spot up shooter (which is possible but he wasn't there the year he played), he isn't the ball handler or passer that Roscoe was, nor does he have the agility (as opposed to speed) to possibly guard a wing.