I think the elephant in the room is the academy and how this board and ownership aren’t getting anything meaningful out of it.
Either through neglect, mismanagement or not properly funded to succeed.
Foden, Saka, Smith-Rowe, Nketiah, Rashford, Mount, loftus-Cheek, Alexander-Arnold, James, and probably more I am forgetting, fill up a squad spot at the clubs we’re trying to compete with, and they generally at worst are useful squad members.
Thus meaning they need to fill less places in the transfer window and can outlay more to get quality in the positions needed. We on the other hand get very little from the academy and buy players that look like they could be good enough but are just below the level required.
Kane came through the academy a decade ago. Winks showed glimpses but has faded badly. Skipp is at a crucial period in his career I feel. Needs to get game time so he can kick on or could be the next near miss from the academy.