It depends how it’s ending. If you accepted an otherwise invalid tenant notice, then their tenancy ends at midnight on that day. If they are leaving by signing a deed of surrender, then its at whatever time you agree.
So OR’s contract says by 2pm on the last day of tenancy. Should they be there after then they are due to pay more rent, strictly speaking.
So I would also say 9am is not an acceptable time on moving day either, I’m afraid. Find another cleark or pick up the keys and do the inventory the next day instead.
A tenants notice has to be a specific length to be valid. If the landlord contracts for an early checkout then the notice can’t be valid as the last day will be less than a full day. I am not sure what a court would make of a landlords claim for extra rent if the tenant stayed beyond 11am in your example.