Figured I'd give an update since I'm going to be at this one for awhile.

I'm working on detailing out the features before adding more appropriate highlights and shadows. I'm still working on detailing out the top and bottom center of the picture, but it's going steady and there's enough variety in things that I'm having a lot of fun! I included the other WIP so you guys can see how I detail stuff I blocked out in colour.

This time I'm approaching things differently by doing my detailing on a single layer instead of pancaking multiple layers on top of each other. I'm finding that it's a lot easier to work on the single layer as I'm not constantly having to switch between layers for minor corrections and can just do it all in one go. I doubt I'd do a single layer approach as a general rule going into things in the future, but for more involved backgrounds I'm finding it a huge time saver.

Once I have all my details down, I'm going to flatten and resize the image by a 100% before redrawing the highlights and shadows a second time. This should really smooth out the rougher edges and make for a cool effect once I resize the redrawn image back to a lower resolution...buuuuut I've never done this before! It should be a fun experiment regardless.

On an related note, I wanted to originally turn this comparison into an animation! I got my whole gif going and everything, but then I realized that the colours were all gif'd up (Hurr, of course). I still have the individual frames, so I might fiddle around with Flash and try it out again in the future.

Drawn in Sai, resized in Photoshop CS6