Its not as simple as Boras gets the best deal and thats where Matt goes, Matt has to live with the deal. Personally speaking, staying on or going to a team that is in the playoff hunt would be my top priority.
There are reasons to stay in Baltimore:
Team is on the rise, great manager, familiarity with staff.....etc
I think that the Orioles could very easily replace his offense for substantially less money than Wieters/ Boras will ask for. Could there be slight drop off defensively? Sure, but as other posters have pointed out, I see Machado as the bigger prize, and he will be the richest Oriole in history if we can get a deal done. If you had a checkbook to manage and you knew you could only sign 2 out of the 3, Machado, Davis or Wieters, which 2 would you choose? Now we know Davis is under control, but he is going to get crazy money in arbitration, so it seems logical to want to sign him. Odd man out for me would be Wieters.....