The Ever17 translation is hilariously bad, so that might be part of it. The fan-translations of Never7/R11 are much better.
As for the choices...
Your inability to make informed decisions about the choices is, in fact, part of the overall plot. The Infinity series likes to play with the fourth wall, although it never actually breaches it; Ever17, in particular, is . The games of the series like to play with , so every playthrough is actually .
The game won't be the same the second time you play through it, and eventually you'll learn enough to understand why those choices matter. That said, I'd recommend Never7 as a better introduction to the series.
So there isn't anything I'd be losing by playing the games out of their published order?
Today's post, Emotional Involvement was originally published on 06 January 2009. A summary (taken from the LW wiki):
Discuss the post here (rather than in the comments to the original post).
This post is part of the Rerunning the Sequences series, where we'll be going through Eliezer Yudkowsky's old posts in order so that people who are interested can (re-)read and discuss them. The previous post was Changing Emotions, and you can use the sequence_reruns tag or rss feed to follow the rest of the series.
Sequence reruns are a community-driven effort. You can participate by re-reading the sequence post, discussing it here, posting the next day's sequence reruns post, or summarizing forthcoming articles on the wiki. Go here for more details, or to have meta discussions about the Rerunning the Sequences series.