If the issue is that Brez values Duran significantly more than any GM in need of an OF'er, then maybe no match up will ever come to be. If someone values him closely to Brez's value, then we could trade him for prospects. Then, we know some teams will trade a 2Bman, 3Bman or SP for the right mix of prospects. They may not be the same as the ones we get for Duran, but we should be able to find close to even value at a position of higher need.
It might be a little complex, but I can't imagine not being able to work something out, whereby we get shut out of trading Duran.
I don't know the Reds thinking, but I think they'd do Lodolo for Duran, and it's Brez who would balk. Would they do Duran + Sandoval (or Harrison) for Lodolo and Singer? The money works better for the Reds than the straight Duran>Lodolo suggestion.
I'm not sure I'd do Duran for just Lodolo, but in theory, our gain at SP2/3 would be greater than our loss at DH/4th OF'er.