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This is really impressive!

For the actual drawing, I'm wondering if the cairo library and drawing model would help. It effectively gives you the move-to line-to curve-to drawing, with some additional capabilities. A simple script around cairo seems like it would cover many more cases, and then this ASCIImage mechanism will help generate those scripts.

What extra capabilities do you think cairo would provide that could be exposed through the ASCII-art mechanism without overly complicating it? This thing is already choosing to not expose the full functionality of the NSBezierPath drawing APIs.

I'm not suggesting extending the ASCII art mechanism. I'm just suggesting that compared to the API shown in the first example, cairo makes simple line-art quite trivial to write as code.

Specific features that would make sense to have available rather than drawing art in an image editor:

Line width, to draw the chevron without having to draw two adjacent lines.

Dotted/dashed lines.

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