It's not about the window of the team only: it's about the budgetary restrictions being placed on him. This is a club that had to ask players to defer money to make an offer to Ervin Santana. That's inexcusable considering Rogers' bankroll, but it's the reality AA is working under.
If he has to overpay somewhat in order to generate revenues and give himself more flexibility moving forward, he has to consider it. You can't simply remove that from the equation.
I never said I'd give up all there for Samardzija, either. AA reportedly favours Price or Hamels. I wouldn't give up those three pieces for any of those guys, but it's a fair starting ask from other clubs. With Hutch and Stroman showing well, I'm not as against moving one of Sanchez/Norris as I was a few months ago. I just don't want Osuna included as a throw-in (Cubs reportedly wanted him or Tirado as a 4th piece a week or two ago).