I'm not sure that Recovery HD is being used. When I boot with the option key down I see 3 options, OSX, Recovery 10.8, and Recovery 10.8.4. I don't believe I have Disk Utility showing hidden drives, so I'm thinking I can delete this Recovery HD from Disk Utility?
As for changing the size through the input box rather than dragging the box down, I increased it from 396gb to 400gb and pressed apply and it DID work. But if I type the max amount (462gb) and click apply. It just goes back down to 400gb...
So do you think I could delete this Recovery HD partition? And any other ideas why it is not applying? I'm going to attempt to keep expanding it 10gb at a time and see if it continue to work until it is at its max capacity.
EDIT:
As suggested before, I appear to have 2 Recovery HDs so may I delete this partition from Disk Utility?
EDIT 2:
I enabled showing of hidden partitions then saw the 2 Recovery HDs and realized one was a outragious 37gb and the other was only ~600mb so I went with my gut and deleted the Recovery HD that was 37gb, it then allowed me to drag my Hard Drive down to 499.76gb and apply it sucessfully. I still have a recovery partition and my Hard Drive is now partitioned to its max capacity. Thanks!