Clearly they aren't committed to Winston as THE future and are more in a mode to give him a shot to show what he can do but, at the same point, if you really think there is a QB in this draft that is a future franchise QB that will be better than Winston, it seems like you don't commit $21 million to Winston in guaranteed money over two years. You sign a cheaper vet like Mariota, Bridgewater, or Dalton and then move up to get your guy no matter the cost. No point in having Winston on the roster for $10 million this year if you have Dalton to start at a much cheaper price until a rookie is ready.
So, I think if they really are doing this to get a QB in the top 5, then the front office is a mess and not thinking logically right now. But, that seems highly unlikely with Loomis, Harley, and Ireland still running the team.
The only small possibility I see is that they really like Willis but know he will take 2 years to develop so Winston for 2 years would make sense. But, that too seems like an odd strategy. I see now way you put Pickett on a team with Winston unless he happens to fall to #16 and you change QB strategy because something unexpected happened. Pickett may never be great, but he is ready to start from day one.