Two things- The BACK TO THE FUTURE STUFF is reaching and even if you think it's odd, it's a huge frigging coincidence.
As far as THE WIRE goes, I wouldn't doubt the man noticed the odd stuff in the BTTF movies and played it up a bit into THE WIRE.
How about this: the Twin Pines Mall and terrorists had nothing to do with the Twin Towers. Showing them in the window was a coincidence, but it's because the guy liked the Twin Towers and how they represented New York so well. His fascination with the towers led to THE WIRE.
And when the Cubs do indeed win the World Series, it won't be against "Miami" so the first part is a big coincidence.
Look for patterns, find patterns. Look for patterns after the facts and make them fit the facts and you will be able to find a way to find them fitting.