The other night I finally got it. XO has been waking me up at all sorts of odd hour of the night. In the daytime he has become far more "clingy." He frequently follows me around to flop down and sleep a foot or two from me.
I finally decided:that his behavior must be ingrained. He sees his job as the night lookout. This came to me when I started exploring why he would wake me crying on the companionway steps. Staying up late to read one night I realized that each time there was an external event e.g. a fish jump, the nighttime security guard patrol/ He would go out, take point, and when satisfied that all was secure come back to lie by my side.
I tried to explore this behavior further but found little data on the behavior patterns of feral cats. It is all conjecture for now.