Great post by the OP
@Lentwood.
I've made this point several times throughout threads on the Caf. We've spent a lot of money since SAF retired, and our issues are not that we don't spend money. It's that we don't spend money on the right players.
SAF had control over the scouting and final say on who to buy. That power was passed to Moyes, LvG and Jose. We learned about half way through the Jose experience that most managers need to win immediately and therefore spend on experienced players rather than engage in squad building for the future. The beginning of the end was when the board came to their senses and did not sanction Jose's request for Boateng / Alderweirald / Maguire. By published accounts, the overhaul of the scouting team and football philosophy began in 2018, I believe.
In retrospect, the hiring of Ed Woodward from a commercial revenue standpoint was actually very good for the club, because he has overseen substantial increases in revenues in the this area. If SAF was still the manager, it probably would have been a decent arrangement because there was no need for a footballing philosophy or a director of football. That was all wrapped up in Sir Alex Ferguson.
There is A LOT of criticism of Woodward in the Caf, with good reason. He's not a football man, and yet, he was allowed to run football operations. SAF retired, there was a power vacuum, Woodward deferred to Moyes, LvG and Jose, and voila, a shiteload of bad transfers.
I blame the board and mostly the Glazers for the deterioration of the squad. They needed to have the management foresight to realize that Woodward was not capable of managing in a way that worked with SAF, because those managers were not of SAF's quality.
Regarding the leveraged buyout of United by the Glazers, it needs to be mentioned that most takeovers / business acquisitions are financed with some sort of loan. The idea is that the profits of the business pay back the loan. Whatever the Glazers paid (was it 750m?), to pay cash for that kind of acquisition size is actually not smart. Also, it was not smart to have such a high interest rate, so that's on the the Glazers.
I'd also mention that the diversified income streams that Woodward has grown and developed are undoubtably going to help us deal with COVID-19 fallout, whereas most other clubs are going to be even more cash poor as revenues will fall even further for them.