Disclaimer: This is not really a reasonable criticism of DD and is not intended as such.
That out of the way, in light of this trade I really wish we could have the Pomeranz deal back.
The system is absolutely in GFIN mode and beyond that, the future is looking very uncertain. All of the Sox competitive advantages in acquiring amateur talent have pretty much been whittled away to nothing at this point. Beyond the top group, the cupboard is fairly bare with no ready road to refilling it. We could be hitting the end of a great run right about the same time it happened in the last century.
There should be room for a couple of titles on the way there, though, but is sure would be nice to still have Espinoza and Pomeranz is now a superficial health question mark.
All of that said, DD shouldn't be expected to be able to predict the future.