CrEaToXx thanks for letting me know I didn't have the latest version, the main link on the Cartographer thread showed 2014.5.22 . Although that didn't quite solved the dds issue. I look forward to seeing your video tutorial.
NPC99 thanks for addressing where I need to find these files and where to put them. I wish that fact was addressed in the Cartographer Wiki on Swyter's bitbucket.
I misspoke on a few things about targeting the module folder, I had already properly setup the module system config and the Cartographer config as you guys described.
Cartographer was able to successfully start after these changes.
Interestingly I read around "The Forge" that Cartographer was more ideal than Thorgrim's map editor, your discussion seem to contradict that. I was actually planning on using Blender.
So what is the best method of entirely editing the world map? I'd want to be on the right track before continuing my project.