Looks great! I really like the look of the awning and also the black finish on the wood. I think the pavers are great too.
I think I would consider getting this built in steel and wood instead of just wood.
As for functionality, I think the benches are in a strange position -- I don't think anyone would sit there facing the stairway and the garbage cans that are in the alley. I would probably just remove them from the plan which is obviously no big deal.
Also, I would change the mailboxes to the locking type we typically use in Chicago.