Parental Controls -- Managed Account Time Limits

My son's MacBook Air is running Mavericks OS X 10.9.3; MacBookAir6,1; Intel Core i5
I set a 2 hour time limit per day and upon the 2 hours expiring, the system logs him off.  Then he shuts it and closes it for the night.
However, upon opening it the next day, the login screen prompts him for a time extension.  It's a whole new day and the 2 hours should start over, but they don't.
Worse, when I go to extend his time to let him log on, it sometimes gets caught in a loop of some sort where it will allow him back on per my administrator password to allow it.  It will allow him on for a split second, then immediately restrict him again saying he reached the maximum time limit and the administrator box shows up again.   The only way I've been able to fix this is by deleting his managed user profile, then adding it in again, once again defining all the parental control parameters, allowed websites, etc.  It's a pain.  I do try to have him log off at the end of his sessions thinking that it will help keeping things orderly, but if the computer cuts him off, I'm guessing that he was automatically logged out and I am not sure that's the case.  It cuts off his time (as it's supposed to) nonetheless.  Overall, it's as if the computer's date/time function doesn't factor in to the parental control settings.   How could Apple overlook such an obvious detail when planning for time limits?   Please, Apple, get these two parts of the OS working together.  So...
Honey-Do List for Mavericks OS X Gurus
Get the Date-Time settings to jive with Parental Controls; kill the loop that occurs when time extension requirement shows up first thing the next day
Create a countdown timer of a sort for managed accounts that keeps the user aware of how much of their logon time is used/still left
Pretty please 
Thanks!

I have found the most common way is simply this: he knows your administrator password. To see if this is the case just change your password (don't leave a sticky note laying around with the written down password on it please) and see if he's still able to get his way.
Also, restrict access to applications like Terminal. Some Google searches could have shown him how to get stuff done through the command line.

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