Idea: instead of matching the shape of what the user has drawn raster-wise, let the user draw an svg-like path, and try to identify the letter by the trace.
Agreed that a pen tool or some type of editor would be kind of nice, but for what he's going for (proving out an idea), this is still pretty fun. I know a little of the science behind it, but it'd be great to read through some well-commented source code. He did link in the thesis on this, however: http://shapecatcher.com/B_Milde%20-%20On%20The%20Security%20...