When Marty first walks into the bank the woman wearing the pink sweater is standing in line. When Marty is exiting the bank, the same woman is entering the bank.
At the Byrde family dinner table scene, Marty tells Wendy that Charlotte is 15. This scene take place in mid to late May of 2017 just as the school year is ending. Charlotte was born in November or December just after Obama's November 2002 election to the Illinois State Senate. Therefore, Charlotte will not be 15 until November or December of 2017 and is only 14 at the time of this scene.
Just hours after Bruce and Liz have been executed, Wendy tells Marty that Bruce did not come home and is missing. How would she know, and who would have told her? This feels a little like adding additional dialogue for the Wendy character.
When Marty is meeting with his P.I., they are walking through Millennium Park. As they cross the BP Pedestrian Bridge, the P.I. informs Marty that "Sugarwood" lives in the Aqua Tower. It then cuts to Marty driving. The Aqua Tower is only 3 blocks north of the pedestrian bridge. When he gets out of the car on Lake Street near N. Garland, he is still 3 blocks away from the Aqua Tower. However when Sugarwood lands on the Street in front of Marty, he has been thrown from the MILA building at Lake and N Garland.
The potential office space is located at 330 N Wabash, which does sit north of the Chicago River (so it looks south onto the Chicago River). However, the windows Marty Byrde thinks are facing south are actually facing west.
In the first few minutes, Bruce tells Marty that Lake of the Ozarks is in southern Missouri. Lake of the Ozarks is actually considered to be in central Missouri.