I have always felt Ben would have made a bold move or two, if given one more year. He almost had to, just to make roster room for all the prospects reaching Rule 5 status.
I have also always felt DD did not have to trade away as much as he did, but since it worked and hardly anyone he traded away came back to haunt us, I was happy with how it turned out.
DD also happened to keep all the best prospects, even with most being lower ranked or with low to no expectations. It may have been part luck and part good organization men advising him, but he did do well on his trades and keeper choices. It's hard to think another GM would have done better, but the Price deal turned into a massive dead money deal, and was part of the reason we got back so little for Betts.
Ben's farm was highly rated but came up short of expectations, so it turned out well we traded away a lot of it.
Much of Bloom's farm is TBD'd and some was traded for Crochet.
DD's farm included players he inherited and did not trade, like Devers, but also many he acquired, like Duran, Houck, Crawford, Bello, Rafaela, Murphy and more.