I think that's possible. Either Hill or Winston will start opening day, and my guess is that the other one will get a chance at some point either due to injury/inconsistency/incompetence.
By the last quarter of the season, though, I could see Payton reaching the point like he did with Charles Brown and Terron Armstead, where he decides if the veteran(s) is going to keep making mistakes he might as well play the rookie because the rookie can at least learn from his mistakes instead of just repeating them.