Hypothetically, if we were to do the Downtown Los Angeles idea, I would imagine an itinerary like this:

9AM (or 10 because of hang over) Meet somewhere at the rim of Downtown. (Staples Center, home of the Lakers/Clippers) I know this parking structure where you can shoot the downtown cityscape from the top floor.

Next, hit the Broadway Corridor:
http://www.experiencela.com/MA_BroadwayCorridor.htm

Next, hit Chinatown or Olvera Street:
Chinatown
Olvera Street

We will eat there since it will be around noon by then.

After lunch, we can jump back into Downtown:
more of downtown Los Angeles
Bunker Hill

Later in the afternoon we can hit Hollywood blvd. We can hang there until the sun goes down for day and night photography.

Then have dinner at Carlitos Gardel.

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Alternate ending:

After Lunch we still spend more time in downtown....
then go straight to the Santa Monica Pier....
Go to Carlitos Gardel for dinner...
Go to Hollywood/Sunset Blvd for night shooting and act like paparazzi!!!

How does that sound?....hypothetically of course.