Here are some general thoughts.

We do FLOWER because flower is nice and wide running one way, we can use a lot of flower, then we go back up one of the other streets sending us back up towards Grand.

I think Olive will run us back up there and send us through the tunnel which brings us to Upper Grand.

 
If we can do this in the first session while Adam is setting up the Hero location that would be awesome. Then Later on at the end we go out again in the Dark.