Noo, good Sir, you went that thoroughly to business at it? Ahh, I well understand your frustration, then. Yeah, your chapter 1 choices do not make a difference to how much Emerson likes you. I didn't want to make it depend on a puzzle. It felt wrong to punish someone for not getting it perfectly, and it also felt wrong to punish players who pride themselves in getting everything right. And besides, although Emerson will tease you if you fail a lot, he's really not a judgmental person. So, for the future, you can trust that he'll separate silly, unimportant things from those that matter.
...and trying out 101-999 influencers sounds like a torment. Sorry, you're likely the only one who knows exactly where the different dialogue points kick in now! :/