So I stopped, and moved on to another project, adding texture splatting to my terrain editor(4 textures, 1 splat map) and am quite happy with the results so far.
I keep making these tools to help learn new techniques. Nudging and tweaking my framework making it a little cleaner and more productive each time. The big issue I have with this is that I've yet to toss everything into a single .exe and see what comes out of it. One day, hopefully sooner than later we shall see.
In the mean time, does anyone have any good book recommendations/links on tool/app development?