I don't see any problem with degradation. I think digital keeps most of the quality of the original, but you're right about some displays rendering the photo differently.
Both of these probably should have been shot in vertical format.
#1 is better because his bottle is away from his face, but #2 has some additional light reflected onto his face, but the bottle is partially obscuring it. This should show you how just a little more light for shot #1 would improve it. You see his cheeks are in the light, but you need more light on his eyes. Not enough to make him squint, but just a little more from some kind of reflector.
Additionally, if you are someplace where you can take off the harness for the shot it would be better as well.
So now you have an excuse to try this again. Take off the harness, hold something like a white tee-shirt just out of the frame to reflect light into his eye sockets (if he is looking just beyond it, the light probably will not make him squint), frame in portrait format. His mother can hold something white and be his eye target at the same time. If you can get him to relinquish his water bottle momentarily, you won't get any orange light reflected onto your model.