I´m trying to measure the total shadow projected from these two elements. The scale level of application must be at the entire city. Not district, not neighborhood, or another scale works in this case.
I suggest you to use the ArcGis extensions, for this purpose. I did it in several occasion in the past years, for professional and academic purposes.
First, you should develop a DTM (Digital Terrain Model), or better a DEM (Digital Elevation Model, different from the DTM because you not only have the terrain height, but also the many elements on it, such as buildings and trees).
Then the Hillshade tool (http://help.arcgis.com/EN/arcgisdesktop/10.0/help/009z/009z000000v0000000.htm) should be the step to do in order to project the shadow generated by the all elements (terrain hills or valleys, buildings, trees, etc.).
I hope this was useful.
Please let me know if you need more details, though on the internet there is plenty of material and tutorials ;)
Cheers,
Umberto
PS
Don't worry about the scale you are considering, as nowadays laptops are fare more powerful than the ones I used in 2011. You shouldn't have any problem even considering matrices of 1x1 metres.
Just to have an idea, in case you're interested, please check the paper I uploaded about the ICCSA conference of 2011, in Santander.