I agree with most of this. I don't think we're too far from each other. We both acknowledge that the Yankees benefit from these advantages, which makes it easier for them to create a good roster.
As for not being able to look at the two acquisitions by themselves, when you're discussing the offseason as a whole, I agree. However, if we're talking about Cashman's ability to complete successful trades, then I think it's fair to look at them on an individual basis.
I'll also address your next post here. When the offseason began, the Yankees needed a number two hitter, a number five hitter, and another starting pitcher. However, they did this, whether it was through re-signing players, signing free agents, or completing trades, those spots needed to be filled. That's how I see it.
And for what it's worth, the Red Sox lost out on Jason Bay just like the Yankees lost out on Johnny Damon. They both offered each player what they felt he was worth, both players declined, the Red Sox and Yankees were unwilling to any higher, and those players left.