Aye - this is it in a nutshell.
AFC's major problem since bosman has been holding onto players - We get what looks a decent team together (see 06-07 season) and as soon as we achieve anything, the star center back is sold & not replaced. This happens again in the following season when three important 1st team players are either sold or leave under freedom of contract, next thing we know, 2 seasons later, derek young is at right back.
Personally i think that this would have happened irrespective of the managerial choices that were available to AFC at the time - the calibre of manager that we can attract to the club is not high enough to convince existing player to re-sign on lesser deal that they would get elsewhere, add to this the idiotic policy of 2yr contracts means that it is virtually impossible to keep a team together - which is what has happened.
Unless the club releases significant funds/wages to keep or replace players lost - it will never get out of this rut.
It comes down to money - which we do not have.