Because they've never needed to run it well. You take over a club with a top manager doing well, with a good structure and it's probably the right thing to do nothing, maybe just maximising commercial activities etc..
So they took ownership of something they'd not had anything to do with getting where it was, so they hold on until the momentum runs out. At this point the cracks start showing through because proper decisions, planning & management have been needed.
But as everyone can see, what happened next was one simple bad decision (Moyes) and everything else is a collapsing house of cards after that, with decisions made under pressure or on the backfoot. With Ole's appointment as caretaker manager, they accidentally made the right decision. Only to then follow it with the wrong decision of appointing him too hastily. There's nothing United (i.e. The club) have done since about 2010/11 that implies this is going to change.
We are where we should be, in terms of planning and vision. You could argue we've over-achieved and should be battling it out to get into the top 6, never mind the top 4. Especially when you see how teams like Wolves are working successfully with what they've got. Granted, it's if Wolves (for example) maintain that next season, it's unlikely they will the season after that. The top 6 will likely come in for players etc.
Focus on the players bad attitudes and/or lack of work-rate is missing the point. It's a symptom not a cause. The club isn't working properly. Some players are overpaid full stop. When you factor in what they're delivering, it's even more ridiculous. Something is amiss and I suspect it's direction and strategy. This translates to appointing the right people to the right posts (coaches etc..) and obviously high profile roles like the manager! Player recruitment would come out of the clubs positive direction and staff/manager appointments, and most importantly someone in Woody's position who knows enough to be able to stand up to managers when needed or trust them. Or recruit them! Seems to me like he's pretty hot on business, but weak elsewhere. Like he's backed/resisted things from managers in all the wrong places, which is going to lead you to not get the people you want/need and then later panic and splurge on people who aren't right. We can think of current team examples of that.
The comeback against PSG (and other performances leading up) show that it's not total doom, but the fact that we could do that only highlights that our default is to under-perform. City, for example, can handle individuals who perhaps have the odd 4 or 5 / 10 performances, maybe even a couple of players, but the team tactics and spirit aren't sunk. A strong plan with a few world class individuals - it's not rocket science! City and Liverpool have had continuity now for a good few seasons - if they'd changed direction several times during that time, neither would be at the top of the league now.
So, what? When the football side of things seemed to look after itself, it did. Everything after that was free fall. Another thing to throw in might be, who wants some of these positions at United? Maybe nobody wants to lead? We're lacking leaders on the field, so why not within the club? But you start at the top, and the Glazers need to own this decline, Woody needs to own it as well. We've changed pretty much everything aside from those 2 things ...
