One of my favorite trolls is @seulgisabs from Allkpop. She swears she's not a troll but in my mind she fits my conception of a good natured, funny, playful troll.
She's never exactly overtly mean. Her trolling is always light and playful and she peppers it with self deprecation and other soft elements. But she's still intending to "play" with the audience.
In many ways I see tolling as a sort of modern conception of the Trickster archetype. They can run the gamut from more benign or playful to more malevolent.