It's been at least implied that making an obfuscation is difficult and a mark of a talented (and perhaps dangerously obsessive) perl programmer. Might it not be a fun and dangerous experiment to crank it up a level of abstraction, and make an obfuscation maker? To bring the twisted art into the hands of the masses?
So suppose some madman were to start from a point of having a perl-aware context engine and something like a text editor ui. From that point you could change it into something like a painting program, allowing the user to draw arbitrarily, and as they draw, rewrite and reshape the text of the program while applying logically-harmless transitions to the text where needed to add more "ink" or to make certain areas darker or lighter. And while it would obviously cost something in performance, there's no reason it would have to change the functionality in any way (unless the performance timing affects the outcome - so you wouldn't want to use this thing on the core of a video encoding engine.)
Maybe while the user is painting, even try to (if this is even possible) arrange syntax elements in a pattern so that in a properly highlighting editor it will show a color image?
Can you imagine the labyrinthine obfus that could be produced with interactive graphical computer assistance? (cue maniacal laughter)
I don't want to be (solely) responsible for bringing such a thing into the world, but I don't mind planting the seed.. thoughts? For example, what transitions might be useful for "darkening" or "lightening"? One that comes to mind for darkening would be.. adding parenthesis around every expression element.