When Jake and Rosa are looking at the security tapes it says that Terry's wife and daughters came in a bit after 12, but later when recapping how she won Amy says that they came in at 9:30 pm.
Captain Holt wears his Commendation breast bar above his World Trade Center Breast Bar. When the WTC bar is worn, it is worn above all other medals, but below the American Flag bar.
The drawers in Jake's file cabinet have no backs. If they did, Holt would not have been able to remove the crown as seen.