Good post mate and sums up the problem here nicely. It is not right for Cortese to have as much power as he does since he can hold the club to ransom if he wants and if he were to die suddenly tomorrow the club could possibly go to hell.
One of your points was that they generally don't need any help with the ladies. I doubt he was doing it because he had difficulty getting women if this is true.
Whilst I agree with your basic point, Leon actually saved the club AND financed the current Ted Bates statue so I would say that his support did the club a hell of a lot of good.