You know what I can't stand the most about his "Gotta catch 'em all" pokemon drawing? I could forgive the color scheme if it were an actually interesting drawing. Bottom line is, the decision of making an illustration with a huge assortment of characters has to be done with some concept of grabbing the viewer's attention, which this really doesn't for me. It's like with any other type of drawing dobson does: what you see is a flat, leveled planed image looking at a bunch of characters that are all spaced within the same area and dimensions. The only reason a person's eyes would be stuck on this image is because of how jarring it is, with little hard to discern characters hiding underneath larger characters. It's all so boring and poor in design.
I understand that working in perspective and coming up with a real bitching illustration is hard, I end up getting artist's block plenty of times because of it. But it's important to practice coming up with unique and captivating ways to draw something to make people go "woah". I've seen illustrations that utilize tons of characters before, and one of the key methods to making the image work is perspective. Compare dobson's drawing to this one:
In it, the horizon of the illustration is much like in Dobson's drawing, but the characters in this drawing are positioned in essentially a diamond grouping, with figures coming towards the viewer while others recede away from them. This breaks up the monotony of the illustration while still making details and characters visible to see.Not every character gets as much space as the next, so to counter act that issue colors are used to make them stand out better. I don't know if I would call an image like this perfect in every way, but it does so much to make for a pretty amazing drawing that it keeps my attention on it.
Dobson just doesn't consider drawing techniques like this for his work, and I'd venture on as to say once his SYAC webcomic came into creation he dropped such things as perspective drawing altogether. This leads me to think that Dobson just doesn't ever look up references or drawings from other artists to get some idea of how to make his own work unique. To him a big collaboration drawing like his "gotta catch 'em all" drawing has no real artistic merit outside of fitting as many characters as he can on paper.