When Nicole (Jennifer Aniston) is at the Horse track she is wearing black high heel shoes but when they bump into the SUV that is following them, she steps over Boyd's foot to press the gas pedal and then she is wearing a nude color shoe.
Milo was handcuffed to the bed in Cupid's Cabin in a different shirt than in the one he is leaving with the cuffs still on the next day. Since part of the bed was still attached to his arm when he leaves, he could not have changed the shirt during the night.
They leave Monmouth Park to go back to New York City, but along the way Milo is tempted to gamble when they pass through Atlantic City. But Atlantic City is close to 100 miles in the wrong direction from New York.
"Cupid's Cabin" is shown to be at Exit 22. If they were traveling back to NY via the Garden State Parkway from Atlantic City, Exit 22 would be 16 miles in the wrong direction (south) as the parkway exits are numbered in ascending order from south to north, and Atlantic City is Exit 38. Also, there is no exit 22 on the Garden State Parkway.
The characters are leaving Monmouth Park Horse track (about 1 hour north of Atlantic City) and headed back to NYC. In the next scene they are driving in Atlantic City. You would not head back South on the Parkway if your intentions were to head to NYC.
Where Nicole lights the road flares in the trunk of the car, a New York Route 135 sign is seen. This is the Seaford-Oyster Bay Expressway in Nassau County, NY. It would be quite the trip for Milo to travel from Atlantic City, through New York City, to Long Island. When Nicole needs to be taken to jail in New York City.
When they go to their room in the Borgata, Milo says that she will be paying for it since he lifted her credit card. However all the Atlantic City casinos require picture I.D. before you can get a room. It would have been obvious that the card was not his.