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2: You can deliver it, but all you receive is a few words of thanks. I don't recall if there even is a penalty to not delivering it. I think the quest auto-completes when you agree to deliver it to Baldur's Gate, and there's not even a marker of who to deliver it to.
3: Oskar is more or less innocent. He might not be Mr. Rogers or anything in terms of being nice, but he's not outright evil either, as long as he's himself
Saving him makes sense because it leads to a quest in Act 3.
No. Roah and the Zhent's at Waukeen's Rest are basically two different cells of the group and aren't aware of the other. Least, there is zero information the two are in contact which does make sense; Roah is working with Absolute Cultist yet the Zhent Caravan gets slaughtered by Absolute Thralls.
I slaughter the Zhent's every run because all I am surrounded by is experience points and dead men.
The quest is completed once you either deliver it to Zarys or agree to deliver the chest. It completes right then and there. You can turn it in to a Zhent in Act 3 but there won't be any reward or exp because the quest is already done likely because the Zhents in Act 3 lose contact with Zarys whether you kill her or not (The Shadowcurse or Cultist on the road probably kill her and her crew) so Act 3 Zhents chalk it up as a lose.
He is an idiot. Nothing like Baelen, not even close. Just an idiot with his head so far up his ass it causes problems.
Act 3 is avoidable if you kill the Zhentarim in Act 1 but it's pretty tricky to get this outcome. Depending of your action with Roah & Minsc (when you free him), you may be forced to ally with the Nine-Fingers -OR- Roah may ask you to pick your side, the Zhentarim or the Guild. The "may ask you" depends if you killed the Zhentarim previously or not and if you spared Minsc.
3) Saving Oskar or not it's up to you. Saving him will trigger Free the Artist quest but there is no real consequence not saving him and treat him as a slave. It's a nice long quest in the city. If you kill him (or get killed in the battle), you will miss some content (and a painting of you).
What I did?I killed the Zhentarim in Act 1, saved and released Oscar to get the quest, spared Minsc but I was forced to help Nine-Fingers. The Zhentarim turned hostile on me because Roah didn't survive my initial attack on my attempt to free Minsc.
I have never, in a single one of my playthroughs, been forced to side with Nine-Fingers despite killing the Zhents in Act 1. I have brought Minsc with me and Roah always tells Minsc to stfu and let the adults in the room speak.
Therefore no Roah to tell Minsc to shut up at the guildhall.