I am a big fan of using maps to convey a feel. I'm not much of an artist but I am rather picky and haven't found an online mapper that has the right style for me. This puts me in sort of a bind. Over the years I've gotten reasonably proficient with Photoshop, but still find it easier to modify content than create my own. I also find it hard to go back and change my mind in Photoshop. Something like making a forest larger ends up being more trouble than its worth and so I decide that it is good enough.
When we talked about core competencies we also talked about critical competencies or things you absolutely want to be present. For me and maps, my critical competencies are that the map have an aesthetic I like and that it is in a format that I can easily change and keep working on.
When I consider those requirements across my various mapping options, I actually settled on using PowerPoint. PowerPoint has less functionality than Photoshop but it is much easier to create content. It takes an awkwardly long time and a lot of experimentation to figure out how to make any given object (i.e. a forest), but once you do it is easy to replicate. More importantly, once created, it is easy to reposition or reshape or recolor or whatever. Because everything is vectors, scaling something up doesn't distort the pattern or texture and so the aesthetic is preserved.
You can download the .ppt here (viewing it in google docs distorts the file but download looks like the above photo). I plan to slowly add, developing a sort of shape-database, over time. Hopefully there is eventually enough that making a map is just pulling pieces together in an aesthetically pleasing jumble and adding names.