What would I consider my comfort skinning (Skin type/design, shading, colouring):
I'm not very good with shading or texture, so I try to make up for it by giving it shape. The hat layer is very useful for this (thanks 1.8, for expanding it to the rest of the skin), and it gives me a lot of room to add the smaller details. I usually make skins based on characters from movies, shows, books, etc, so accuracy is also important to me.
Why do I enjoy making skins in this comfort zone:
I like it because I can make the skin look good, despite the lack of shading.
Have I ever considered breaking out of this zone to try the complete opposite of it:
Not out of this zone as of yet, but my much older (and thankfully unpublished) skins use techniques I'm very glad I've left behind. Colour was almost always violent and clashing, using an extremely limited palette, for example. At the very beginning, I had convinced myself the hat layer (only usable on heads at the time) could only be usable for actual hats. Very glad I've been experimenting outside of that. Hat layers are very fun to play around with.
What kind of skins do I enjoy seeing the most:
I love seeing skins that do well at portraying what they're trying to show, that have a good palette, and make use of the hat layer. I don't like many of the first skins that show up in a search, because many of them have just been around longer, before the 1.8 format. Leads to some very overdetailed skins, that look like a shiny mess of different palettes thrown into a blender.