I think you're denigrating what was and romanticising what might be tbh. Not massively but more in an expectation that things could be very different.
To play family fortunes for a minute....what would move us higher in the league and closer to cups?
Top answer by a some way ....more money.
Then followed by ...the big teams having an off season.
DL has tried things and some (with hindsight) have not worked 'Win now' manager (ok maybe a bit of foresight with that one

). But since Paratici and Lange have been on board, most would say our transfer work and strategy has been very good. I'm not sure if selling players is DLs fault or a market problem?. I think the low wage ratio level is logically partly because of the stage of squad cycle we are on. Transfer spend has been good, partly helped by the lower wages as it all comes out of our finite funds.
Loads of the in detail of 'how we do (or did) business' is hard to really comment on as we just don't know. Whether there's more to be leveraged there is guesswork, and even if there is, it's family fortunes top answers 1 and 2 that really shift the needle.
Ive said before that if we are smarter and things come together, department wise, recruitment wise and probably (to some degree) lucking out with a excellent manager (like Poch), we can have a moment knocking at the door. Perhaps the beginnings of that is already happening right now with TF?