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I really only think of the first two movies as being "real" Hellraiser movies. The rest just don't fit with the mythology and lore put down by the first two so I try my damn-dest to disregard and forget about them entirely.
Given Pinhead's actions in the first two and especially information in the Books of the Damned comics, Pinhead is neither good or evil. He just is. He is a "soldier" of sorts for Leviathan. He is also an embodiment of Order (the Nightbreed were Chaos.) To the utmost degree that when a young Cenobite suggested they attack the Nightbreed earlier than planned because they were in a weakened state, Pinhead pulled out a huge tome and said that they couldn't attack now because it was written that they would attack in 2 years, 4 months, 17 days, 3 hours, and 52 seconds (or some equally exact time, I can't remember the exact time from the comic.) Which is also why I loathe the third movie. With his human side removed, Pinhead turns completely chaotic and kills randomly. It just doesn't fit.
So while Pinhead is most obviously not "good," nor is he even a "dark hero" (Kristy did basically con the Cenobites into helping her for her own ends) I wouldn't necessarily call him "evil" either. Especially from his own perspective, which is really all that matters when it comes to discussions about good versus evil. He just simply is doing what he must do.
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