As someone else asked (but you didn't quite address), there aren't too many key holdovers from the Wade era, so it safe to assume that Felix, Jenkins, Scandrick, Rat, Spears, Sensi, Ware, Romo, Spencer, Witten, Free are the guys who Garrett will eventually be moving out or, at least, looking for their eventual replacements?
To me, I think it's a given that Felix, Jenkins, Rat, Spears and Free are 90-100% gone.
I think Scandrick, Sensi and Spencer are on the fence or very soon to be gone (within the next two seasons) with Spencer being the one wild card.
Finally, I think the team (read: Garrett) likes/needs/appreciates Ware and Romo but realize that they may be getting long in the tooth and that they would sooner rather than later find their replacement. I also think they may HAVE to keep them given their vital positions, but would rather go in another direction if circumstances allow.
Finally I think Witten is the one guy they'd prefer to let retire a Cowboy.