The boat is gonna sway too much when you cut out, in turn washing out the wake- completely undesireable. Towers and poles are typically at their most effective height; tall enough for more air and not too tall to sway the boat. Ten Foot Pole makes pylons, and their original designs actually were ten feet high, but they shortened them up when they realized how destructive it was to the wake.
At least that thing with the sail would counter the force of cutting out and not sway the boat.
Basically, I hope this is just a joke... and that pic doesn't look functional- the extension would just snap off (unless i'm missing something in the pic)