I think rebuilding is mostly down to the quality of decision making. Clubs that consistently make poor decisions like North Melbourne will do so even if they had more money and more picks.
For example, the decision to hire David Noble as head coach who had little to no coaching experience is an unforced error and it doesn't matter how many free agents they have access to if they make that sort of major decision
Also, the choice to ignore certain types of player at the draft (eg choosing Phillips over McDonald) has had major ramifications for the quality of their list. Giving them more picks to fix picks they stuffed up isn't the solution, it's making better choices with the resources they have.
David Noble didn’t need anything that Paul Roos could offer, can’t have been much wrong with him.