Quarter I Project - City Scene

For the first quarter of the new school year, I hit the ground running with a new project. With a lot of ideas floating around my head such as a 2D walking character, an explosion, a 3D walking character, etc., I finally settled down on my newest idea: a city scene.
There's almost no easy way to jump into modeling an entire city. For the first hour or so, I just examined the downtown areas of many major cities including Detroit, Chicago, Kansas City, New York, Denver etc. I just wanted to see what my final image should look like. I decided to take a building or two from many major cities. I had a slight interest in architecture and designing my very own city has also been something I'd've felt I enjoyed.
I have this desire to create, so of course, animation felt fitting. But I also had the idea to create different settings, not just characters. I want to show somebody something that I can be really proud of. However, I also have this dystopian society in mind. I'm basing my project off of Detroit, a city that has been absolutely destroyed the last 40 years, but still coming from my own mind.
Like every good project manager, I needed an outline to follow. So I drew one up:

PRELIMINARY DEADLINE:
August 21st, 2014: 
1) Look at different downtowns and get inspired - 1 Hour.
2) Place a city map on top of a plane to begin - <10 Minutes
3) Start putting streets down onto the map. - 2 Hours.
4) Finishing putting streets down onto the map. - 1 Hour.
5) Start sculpting buildings.
FIRST DEADLINE:
8/29/14
Have all buildings modeled in a rough design. Does not have to be perfect.
SECOND DEADLINE:
9/12/14
Have all buildings completely finished. Try to be as done with this as possible.
THIRD DEADLINE:
9/19/14
Have all streets textured and have some small details started (streetlights/mailboxes/trashcans etc.)
FOURTH DEADLINE:
9/26/14
Have most of the small details laid out and finished.
FIFTH DEADLINE:
10/1/14
Have all small details finished.
RENDER DEADLINE:
10/6/14
Be sure you have everything textured!
FINAL DEADLINE:
10/9/14
End of Quarter. Have project turned in.