Now I'm up to today. Was considering scale. I had an idea about how big I wanted this to be, but I needed to know how features should be represented at that scale. Took a look around Google Earth and Nova Scotia Canada caught my attention. My island will be about 400 miles wide I think. NS is about 350. Then I found http://www.novascotianature.com/habitat.html and was pretty happy with the diversity of its nature and landforms. A precedence is set, so I feel I'm moving in the right direction.
I also read CG Guide on Fantasy Cities 2nd Ed by R Shankar I found here somewhere (sorry I don't have a link if someone recalls how one can grab that). I'll try to review it again before I post a final map since I think there are things I'll need to be mindful of. A great read on urban development and representation, though I think at my scale, that won't come into too much play.
I'm a bit reluctant to move further because here is where the real learning curve is going to be coming in: brushes and artistic representation. Paint.NET is all I'm really comfortable with, but I think I'll have to move out of it before it's over.