I think this game could be best executed as a tablet game, by drawing the circles freehand, and/or tracing for easier modes, maybe. However, chalklings could be premade, with preassigned stats or, like previously suggested, you could draw it before hand and get points based on complexity. A system that let you progressively 'discover' more defenses could be implemented, and a skill upgrade tree could be used, like previous mentions, to specify in which ways you would like to advance.