@fskn: Thanks so much for taking the time to edit and for the words of encouragement. After a five year hiatus, I'm hoping to be more active in the PA community.
- You definitely made the lantern brighter than I had intended but I think somewhere in between is ideal, so I am working towards that. Thanks for giving me a better idea of where the light would hit.
- In regards to the robe, I just have to admit that I am handicapped by not really doing any real practice on drawing / painting cloth. I want it to be rippling a bit in the wind (notice the direction of the grass), but my brain simply shuts down when I try to model the physics in my mind. Ultimately, I just need to imitate references for hours until I get a 'feel' for how fabrics work. But for now, I'm just throwing stuff at the wall and seeing what sticks.
- Good idea about the moonlight on the edge.
- Your trunk looks a bit flat, perhaps, but I think you nailed the texture. I will try to emulate this while trying to find a way to make the trunk look like a cylinder.
@eliddell: Thanks for the feedback!
- The figure is supposed to be wearing a mask. Ideally something like a venetian mask (without a mouth) but I'm struggling to make it readable without making it comical / cartoonish.
- Thanks for your comment about the middle. It was indeed supposed to be cloud.
- I'll need to think about the most distant buildings blending into the sky. I don't really have good intuition when it comes to atmospheric effect at night. Adding a highlight doesn't make sense to me, because then the building is brighter than the background and has more contrast than buildings that are closer instead of having less contrast and blending more into the background sky. This feels wrong. Of course, there may be other issues I'm not considering.

EDIT: Now SeinRuhe has gone and posted another great edit while I typed this and so I have to reconsider everything, including my life. Fack. To be continued.
EDIT2: Here we go.

@SeinRuhe: Thanks so much for taking the time to help out with an edit and thanks for the compliments!
- Unfortunately, my idea was to show a fictional setting of a medieval city above the clouds. So while I love your idea of making the character stand out, I'm not sure how to do this while still getting across that the plains are made of clouds. On the other hand, I may have already failed, since nobody seems to read them as clouds anyway!

- While you suggested I should merge shapes on the right side of the character, I've gone ahead and added more shapes to make the character more interesting. Now I feel dumb and very conflicted, because I like your design.
- Interesting point about harsh speculars on the robe. I was trying to use the highlights to make the character stand out more, but I guess I went over the edge and made it kinky. I will play around with this. Wait, that sounded wrong.

- Great advice to check my values. This is one of the disadvantages of being stuck in the 90's and pixelling with MS Paint. But I'll do that in the future!