Probably, but they are much worse at buying players which balances itself out.
The illaramendi transfer has been a total failure from the moment he was bought to moment he was sold.
RMs transfer buys bad? We've been making humongous revenues getting money back for stars moving on (Ozil, Higuain, Di Maria, Morata.. kind of..) and made very smart buys/loan moves for small money (Adebayor, Essien, Chicha, Carvalho, Callejon, Carvajal). There were very few transfer busts since 2009 where we splashed out and got very little or zilch out of the player (Kaka, Sahin, Illarra). Nearly all other 10-30M transfers were very effective pieces of business.
As for Asier, no, he never got played at CDM. Only one game and one half kickstarted and decided that - Dortmund. Whether it sat in his mind since or not, he's never been anything worthwhile since. When a manager prefers to start Ramos at CDM over you, you know you're a waste of everybody's time.