This is not difficult. You have a team that has a core of very good players for the next 3 years (for most of them). You have a lot of interesting pitching and position players coming up in the farm system. You can spike the payroll a little now, with the expectation it will level off or slightly go down without hurting you. Therefore, sign Cole now (unless the price goes above $250 million for 7 years, at which time you are talking crazy money), QO Oderizzi, he will probably either take it or work a contract for like 3/$45, offer Pineda like 3/36 (this is a risk, but I feel it is fair)(he was on his way to much more before the suspension). Sign a couple of decent bullpen pieces (Romo, and one other(Smith, Becentes, Watson(if you're worried about the money))). Call it a day. Hold reliever contracts to 2 to 3 years. If you fail to get a front end starter, then get 1 of the middle pool (Wheeler, Bumgardner) and hope to develop 2 - 3 of your own. Would hope Oderizzi takes the QO, you will probably know more after 2020 on the development of the farm system pitchers.