It all starts at the top, with a CEO who's great and making commercial deals but who doesn't grasp the club isn't just a brand with a balance sheet. Woodward's job, technically, isn't to win titles, it's to increase revenue and raise the share price which is what a signing like Ronaldo does. You can tell he still hasn't learned from the Klopp Disneyland debacle.
It's why they need to make big signings like Pogba, Lukaku, Sancho and Ronaldo without actually addressing what the issues are on the pitch. At the same time, that lack of direct experience and the sentimentality of the fans make Woodward vulnerable to the United old boys network, which is why it's been so easy for Fergie to get the likes of Giggs, Carrick and Ole jobs despite their lack of experience or relative expertise. Phelan's still there too. There's been talk of getting a director of football in but it's incredibly telling that the names touted have all been ex-players like Ferdinand.
They look threatening every now and again, especially when they go on a buying spree, but apart from Fernandes and initially Maguire, no one has really made much of a difference. I'd disagree with Lobo's assessment of the players. Lingard for instance went to West Ham last season and immediately looked twice as good, as did Lukaku and Smalling as soon as they left. There are definitely the raw materials there for a great spine, but no matter who's manager I can't seem them progressing as long as Woodward is overseeing things and Fergie has a prominent voice.