Thank you for your feedback. Really have not decided what I am trying to do. I have a few adventures adapted into homebrew locations and thought I could let it just expand naturally. So basically I am laying out the world but what that will actually looks like will come from the other players (but with some boundaries to work within). Actually every line is from the real world and have a meaning to me. No Iceland, not really great lakes (but NYS), no Nile River, and sometimes my lines were exact and others exaggerated. I like you suggestion of going back to the places and see about grabbing some more detail other than the coasts and boarders.

Of course the more I think about the areas that are nagging me the more likely I am going to increase the size. I think my next project is to add a grid to help me show possible scale (although I dont plan on getting a map to exact scale just using GIMP, would need ArcGIS for that) but I have experience plotting on maps so it will help me determine what could be realistic within the DnD environment.