The flag on the side of the yacht club building near its entrance is the burgee for the Sidney North Saanich Yacht Club in Sidney, B.C.
The aerial shot at 1:16 into the movie is Menemsha Basin in Martha's Vineyard.
Minute 55:55 Jeff says, "Hey Gus, do you have a second?" Gus replies: "22 million 75,000, according to average life expectancy... I can offer you a couple" Actually 22,075,000 seconds would correspond to 255 days 11 hours 56 minutes and 40 seconds. Perhaps the correct number could have been 2,207,520,000 which corresponds to 70 years.
Jeff Jackson's birth date is shown as September 16, 1985. Assuming that this movie takes place in "present day", that would make the character of Jeff approximately seven years younger than Jesse Metcalfe, whose birth date is December 9, 1978.
Jeff was forced to retire from the Boston PD due to a gunshot wound to his back bone.