I think he's already ahead of the likes of Pennington as he broke in younger and has games where he has excelled. Galloway I always found an odd case, and probably struggled for the change of manager.
Osman was a very good talent, but after his 2 big knee injuries there were some doubts about him. I don't think Moyes had him in his plans at all, but he kind of forced his way in.
I think he lost his way a bit this season. Some time away from the game, to grow, rest and think is never a bad thing. If I were him, I'd be doing everything I could do be in top shape for pre-season and try to start with a bit of a bang.
As always though, and as my dad would say, there is always another "cab off the rank". Lewis Dobbin should be fit and will certainly be looking to make an impression, and young Whittaker is a similar type of player who has made a very handy impression at under 23 level. This summer is the one for Gordon to make that impression or he my find younger players just push ahead of him.