I agree with many of the points you're making here. I also think The Wire is the best show ever done. I re-watch every couple of years.
I think you're partly right about the difference between Barksdale & the longshoremen, but isn't the main reason the longshoremen are so careless, as intended by the writers, is that they're not professional criminals? Wasn't the idea that they turned to crime when jobs dried up?
Granted, you might say the same for Barksdale. It was Mario Puzo who pointed out that there are always people who won't accept second-class status in society, & will turn to crime if other doors are closed to them. Like the longshoremen, he wasn't going to flip burgers to support his family.
Still, Barksdale & Co had a vaster background from which to draw expertise in avoiding surveillance by the authorities. And yes, I agree that's largely because people of color are always under greater surveillance than whites.
About the Capitol riots/insurrection, yes, it was privilege in general, but it's also evidence that Trump is guilty of inciting, because so many believed they couldn't get in trouble because the prez told them to.
Also because many were just fucking morons...