5:15 PM - 6:00 PM: Looked around some a bit after work and figured out what the problem with the nil class was that I was having. Apparently you need to have your file owner as something specific, in my case NSWindowController. Then you need to attach the "window" property to the window in question. Once that happened, the window was then redrawn. I spent about 30 of those minutes talking about what I had learned last Saturday to two co-workers. Slow going so far.
8:00PM - 8:45 PM: kids headed to bed after dinner and a family discussion about baptism. (My oldest daughter will be baptized shortly) Time to implement what I learned right after work! That wasn't too bad, also fixed up drawing our window to the appropriate context. NSEraseRect() always fills white, [NSColor clearColor] and NSFillRect(rect) work quite well to clear a drawing area. note to self, when setting bounds you want to set the frame, not the bounds of a CALayer. Setting the bounds doesn't change the frame size. Taking a break, my eyes are burning. One major milestone accomplished, something that works! Wohoo!
10:15 PM - 11:00 PM: After talking with the wife about the app and some possible vacation plans (not related, heh), I realized that we don't have to do a custom moveto -- you get that with the ordering of coordinates and checking to see if the next object starts from the last location. Nice! Also explained how the editor will work as my wife will theoretically be helping me use that in content creation. Next stop will be creating the tools that make the points and then save/load functionality. I may have to mess with undo/redo as well. Actually probably.
11:00 PM - 11:15 PM: AARGH! So I've been spending all this time writing an editor. I figured out that some (old) apple code does exactly what I need minus curves and saving to my custom coordinate system. It's a sample called "sketch", 2 versions located here and here.
I've also archived this code in my "sample code" folder. I will be using this as a foundation for sure! This cuts out a lot of dev time and will be immensely helpful.