When you tak a step back and look at the direction the FO is taking I think you are starting to see a trend, There is a 2 prong approach given the current state of the team.
1) The signing of McCann and Ellsbury takes hem to the 37 age bracket roughly and not beyond. Maybe with an exception for a sure fire, first ballot Hall of Fame player (Jeter example) then you go long term, however what I am seeing and the new dynamics is this. Say most players come to the majors at 23 to 24 years old for the first time. A huge amount need to make an adjustment and may go back and forth for a year till they are more ready. So under team control for the next 5 to 6 brings them to the 29-30 age range, and now they are established with statistical data to support their value and warrant the first free agent contract and the Yankees need to be consistent on the 7 to 8 year commitments that they make and put the productive threshold of most players at 37-38. You will always have the exceptions on both end of the age group, for example, Trout and Kershaw because of age and performance will get the 10 year deals or able to double dip into free agency like Arod did. On the other end, you will have a handful of players per say like Beltran, who will be productive past the curve and because of need you risk a 3 year deal with.
2) It is necessary to develop players at a minimum at least. I feel they should specialize on high skilled positions for non pitchers. What I mean is this, SS, C, CF skill sets that if developed are always in need. So instead of the best player available, best player at those positions available in the draft and International signing. Look at this past year, You had Profar, Iglesias, to use as pawns, I know I am forgetting another one, but get my point. In all of MLB, there is always a team looking for a C, SS, CF type. You then can use as trade chip to fill your needs and keep away from the long term free agent costly contracts. I know it's not a perfect world but it's a plan, rather it's the Yankees plan, then who knows. And this goes without saying you try to develop pitching for yourself, cause you can never have enough pitching.