Well, ABC ... here I go again .. being contrary. I love this kid! He looks like a actor out of a wholesome 1950's sitcom. I think the pose is perfect. Nothing fancy, just a head shot of a good looking kid, typical of that time period. Now I know this Murdoch day is celebrating an inventor from the late 1700's but this kid could be right out of a Charles Dickens novel as well.(Maybe a bit too well fed for that time period, but so be it.) So for me the impact of this shot is excellent.

That being said the technical really suffers. If you're going to submit it, you've got to get rid of the shadow-light thing on his face. The fill flash you used did not do it's job. I saw your second post where the shadow has been lightened, but you lost contrast and the light is still there. I am sure this could be fixed in post by someone who is very skilled. I would definitely ask for help in the Post Processing Section.

I am not a portrait photographer but based upon my experience, I would call this merely a snapshot. The posing is what kills it for me: head on. Furthermore, the tight cropping removes any other compositional elements that could have helped the boy. Two excellent examples of effective head-on posing are Kharasch's portrait of Churchill and Hemingway.

I do not like the lack of contrast and how the shadow falls across the face. The rework posted separately was a leap in the wrong direction.

I encourage to submit this to your camera club so that you can get more advice on how to approach portraiture in general and this shot in particular.

Well, If I were the judge this would not do well. There is virtually no contrast - just way too flat. The on camera flash - unless used purely as a very light fill - will never, ever give good results.

You should at least try increasing the contrast a bit with Levels or Curves, but I am pretty sure there is not enough contrast in the original to allow that to work.

The sun hitting his ear and cheek could have been easily avoided if he turned his head just a little bit to his right.

This is an OK snapshot at best.

I think this is a big improvement. Still, I think you could go even further in the same direction and keep getting better. This boy's eyes are so sparkly and expressive, they beg to be brought out. And now that you told us the smudges are engine oil, they deserve to be seen more clearly too. I took the liberty of downloading the photo and fiddling with it, and even the jpeg held up to more brightening/contrast/clarity/blacks and the eyes and expression and texture (hat, freckles, smudges) really came forward.

I really like this portrait despite the lighting challenges. You have a gem here, regardless of how you choose to present it.