Correct, it is also over looked that he was never a rich man himself, so was not using his own money but the money allocated to him. Much easier for the family who actually own the club to say "we will be spending more" than it is for the man tasked with running their company.
Also I think all of this talk always over looks where we came from at the time DL took the reigns to where we are now, all the arguments about ambition and success in the transfer market comes from a base he grew, raising expectations. There is no way in 2001 the same fans would have been arguing for parity with Arsenal, Liverpool, Bayern and Dortmund. And equally, I find people only ever compare us to clubs based on their hugely successful moments, not their bad.
For a club that has won 2 league titles in its life I do find some of this laughable, you can be ambitious, but also being realistic isn't the crime its made out to be. I went down a Hoddle rabbit hole the other day and it re-shocked me to realise we won 3 major trophies in his 12 years here, 3, all coming over 3 years, so for 9 years we did nothing, over a period fondly looked back with him and players as the "Glory Glory" times. Don't get me wrong, I absolutely love him and that period too, but again, it wasn't exactly prolific success.
The guy made massive mistakes here, but he also most certainly raised the expectations of the fanbase which for me is a marker of his success.