Start with the paint-pot tutorial I gave a link for. For finding if the student hits a wall, look here:
https://groups.google.com/forum/#!topic/mitappinventortest/J6b8eVGcP54(Tracing the letter is like solving a maze)
You need to find pictures with letters on them, where the letters have marked borders or have an even color.
I think it will be not so easy to find out whether the student completed the letter correctly. Maybe a visual check is needed, at least for your first prototype.
Try some blocks and report here if you have questions.
Cheers, Ghica.