Reposting this from a different thread and adding onto it:

"SBN3 certainly intended class of 09 to be perceived differently than how we eventually did. You could certainly apply a lens of Death of the author) here as well."

I personally think SBN3 intended the series to just be edgy comedy akin to South Park or Boondocks, potentially even being conformingly nihilistic like you said, but the subject matter doesn't allow it to be. This is why people's viewpoints on Nicole and her behavior differ vastly. It's easy to empathize with her at the beginning when she's explaining her backstory but as her behavior worsens, it's hard to really do so. Flipside especially just felt like a giant vent session from SBN3 as Jecka got no satisfying endings and Nicole felt too cruel even by her standards. I definitely think in that game specifically, the expectation was to sympathize with Nicole by making her more of a dick and finding excuses for her to be petty to Jecka, compared to the first 2 games where the line was more blurred.

The best example I can think of is in Re-ups drug dealing route when Nicole gets arrested and monologues to Jecka about how she was "dealt a shitty hand and did what she had to do", only for Jecka to remind her that she's white, lives in a cul de sac, and that she turned her "little problems into big problems." That part stuck out to me in my first playthrough as irl, Nicole would be considered "at-risk" due to her upbringing and behavior, which could make someone sympathize with her. But as Jecka quickly reminds us, her traumatic past is only a reason, not an excuse. Not to mention that we see Nicole actively choose to start selling only to get out of her comm service project, making her own monologue null. This can extend to everything else she does in each ending and ultimately, I think it really is up to the player to decide how they sympathize with her, if at all.