But what’s the end game? I seem to recall he fought pretty hard to prevent the purchase from going through and only when faced with a lengthy court battle that he would likely lose did he accept. And he is in for a fair amount of loss on that deal anyway.

Isn’t it a simpler answer that he is just incompetent and somewhat like sand, the more he tries to squeeze the users for money the more it slips through his fingers? The strategies he’s trying might work in other business types like the car industry but not one where it is wholly dependent on user content and engagement (and the ability to engender enough good will to sell ads)…