I would say after another few hours of practice I am getting a lot more efficient with using the select and refine edge tool in Photoshop to the point I feel the look I want will be achievable.
I continued practicing on the street scene but found that now I am quite comfortable with selecting the people the shadows are become a point of frustration as the people are sticking out because they are lacking some interaction with the background.
I have added four people to this shot who are all looking at me in my direction. As they are an overlay the backgrounds are not a problem but the floor below their feet is. Even though they are all taken in the space of about 3 minutes the lighting and colouration of the floor changes enough for them to stick out. Also You can notice the guy on the left and back are the ones where I didn’t attempt to take the shadow and they look pretty bad. On the other hand when I tried to take the shadow I was able to get a much more lifelike look.
Dealing with shadows I am sure will make me feel unsatisfied as I know it will never be perfect so I decided to look at examples where this would not be a problem.
I found a number of shots that are waist height and if I combine that with a background which has depth and someone in it looking at me this might just be a better way to go. The key now is to find all my shots which could possibly work in this way so that is my next move. I am also a little concerned about the fact that by shifting the people around in the shot their eye line will be off the centre and maybe will ruin the feeling they are all staring at me. I am however quite happy with this example and it gives me hope that this project will work out well.
David Leverett 
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