Okay. Here I was ready to finish my winning entry to this contest when I realized that Tom and Huck needed some serious shadows. Now I've used shadow layers in the past with some decent results. Others here claim all shadows are painted in by any self respecting chop artist.
Now as you can see there is a color overlay that has been cut from around the two subjects. But no matter what I tried I could not match the color or density of the image, even after cutting the color overlay from the shadows.
These are well defined shadows and to match them the subject shadow was going to need to be defined as well.
I'm stuck. And since I'm not entering the chop I figured I could post this now. I'm very interested to see how someone with more talent would tackle this shadow dilemma.

I usually take the image that creates the shadow, in your case Huck and Fin, and make an outline shape with them on a new empty layer. Then I fill in that shape with the paintbucket and the little pipet, matching the black/gray from the shadow on the boardwalk.

Then I go and play with the shapes, flipping them, and shrinking and warping them, untill they look the part.

Make sure in your case that you not only have the horizontal shade on the boardwalk, but also the remaining shadow of the head and shoulders on the fence to the left.

You should be able to caculate the hight of the top of the head shadow on the left fence from the angle and hight of the right fence shadow on the boardwalk.

But, in case you only were interesting in the colour dept of the shadow, pipet and bucket into an outline of your original figurenes, and then, when you have placed them, look at the outline, and see if you need to soften the outline to match other shadows.

That is how I would have worked.

Well isn't that the about the same as creating a shadow layer, transforming it and changing the "fill" to the layer below? I kinda see what you mean by using a pipit to match color though. Changing the angle to match the surface isn't such a big problem. It's getting a shadow that is defined and of the exact color of the source. maybe I should have left my color layer to the end of the project, though It seems to me that cutting that layer out should have the same effect? Or maybe I should go back to mowing grass? Who knows?
I liked the video. But science and progress will never lead to individual happiness. That comes from God and enjoying the fruits of your labors. Even if your just laboring in the shadows.

I see what you mean. Lining up the shadows layers, isn't the big problem. However, getting the color, tone, and boardwalk texture correct, is a larger problem. I would have probably preferred to work in black-and-white first, adding in the shadows and then convert the composite to a color image.. Just a thought.

nice to meet you.