Hahaha yes! Even if I just said how impressed I was by your more realistic drawings, my first love is for goofier characters like this!
That said I think your dragon needs the same treatment--your hero clearly benefits from your experience with more realistic characters, but the dragon is kind of plain by comparison. Whereas the hero has very silly proportions and features, the dragon is also strangely proportioned (super-thick neck, but very tiny wings!) but it doesn't look as intentional. Just like you did with your humans, I think you'll benefit from doing some more "serious" creature studies, too!
I didn't like the wings too. Dragon wings are usually drawn like bat wings, which have aproximately the same structure of a human arm. In my drawing, the wings were made from the "forearm". It lacks the "arm" and "elbow" structures. Maybe that's why it looks smaller than it should be. I've already realized that, but it was too late, for it was already inked when I saw the mistake. Also I don't feel comfortable drawing characters from the back. I totally miss the feel of proportions when I do it.
I know what you mean about drawing characters from behind, it can be really awkward! But I do think some of it is really successful, like the head looks really natural to me (even though its eyes are obscured. It's especially cool how much of the mouth is visible.
I actually think in this context (alongside the hero) nonsensical wings that don't have any kind of real-life basis (ie, arm/elbo bone structure) are just fine, they just need to be positioned better. I just think the dragon should be as "extreme" as the hero is!