His behavior sounds both attention-seeking and playful. That's probably how it began anyway. Now, after several years, it's probably both attention-seeking and a well-ingrained habit. Even if you do pet him daily when you go out to the barn, for such an affectionate-sounding, people-loving cat as he is described as being, (a "love" and wanting to lounge with you in the hammock, etc.), he probably feels it's not enough. It sounds like he craves your attention, even if it's negative.

I have to admit, I don't know how to go about changing such behavior in an outdoor cat, because you can't necessarily correct him and then remove yourself or him from the situation like I would suggest you do if he were indoors. If he were inside he would feel more secure about his place in your life and that would probably help a lot, but I know many outdoor-only cat owners don't go for that suggestion. Perhaps someone else will have an idea for how to use some behavior modification techniques on an outdoor kitty.

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