My view is that Woodward isn't doing such a bad job intentionally, but both he and Matt Judge are hopeless negotiators and evaluators of talent and player worth.
That coupled with the passive indifference of the Glazers has culminated in the destruction of the roster and the clubs elite position in the past 6 years. As many have said, look at their other sports franchise, Tampa Bay Buccaneers, to understand that they have no strength other than extracting value.
Woodward and Judge are both bankers, yes with a b, and until there are experienced and high quality football administrators on their positions, it's unlikely anything will change.
Those of us that have followed the club for decades, see no light on the horizon until changes in administration are made, and a change in ownership wouldn't go astray. Some of the blame has to go to Ferguson for letting the club drift in the last few years of his reign to possibly appease the new owners. There was no regeneration of the roster to younger players and his idea of value saw him trapped in his own thinking.
Not a good outlook for at least 3 years, and if Ole doesn't undertake root and branch reform of the roster, or will he is allowed to, uncomfoartable times ahead.