I want to weigh in on the student title issue specifically, as someone who is fluent in Japanese but was unfamiliar with this game until this patch came around. It seems that the format used for the Let's Play is "Super High School Level ____." And the one used in this translation patch is "Super Duper High School ___."
The Japanese is 超高校級の「◯」. It seems obvious to me that the point of this phrasing is to illustrate that these are not ordinary high school students, but also to give them a descriptor. A nice little box to fit the character into. In Japanese, 超 can be used in contexts that words like "super" are not in English. In standard, non-slang usage, It's used to emphasize that something is way above the norm, for example, 超高層ビル for skyscraper. In the Japanese, it's clear that the intention is to emphasize the "high" in high school, but "super" has very specific connotations in English, and they are by default gratuitous and goofy. That may have actually been the intention (the slangy usage of this is much more in lines with this, after all), but it may not have been. I'll defer to anyone who's more familiar with the franchise than me on that one. I think there are a number of directions that can be taken with this though. Could be as simple as "extra-high" or "exceptionally high" or "extraordinarily high." At minimum, though, I think it should be written as "Super-High School" to make it clear that the super is modifying the high, rather than the school.
Next, in Japanese, 級 is a suffix used to denote the grade or rank of something, although its reach is a bit different than those words in English. Although we do use "level" to refer to ranks sometimes in English, in this case it seems very awkward. I guarantee that anybody who sees "Super High School Level" at first is going to think that it's referring to an actual level in a game or something, rather than a student rank or classification (in fact, someone in this very thread thought that only the "Super High School level" of the game was translated, and posted disappointment). In this case, the pattern used 高校級の「◯」, makes me think that what they're actually going for is something along the lines of "class ____." "Class clown" for instance. To borrow the familiar translation, "Super-High School class Idol" would be an example. Also, most of the titles in the game are occupational nouns like "wrestler" and "author." This is why I think the fan translation was on the right track with Naegi's title, "Super Duper High School Luckster." I understand that before this, the common translation was "Super High School Level Good Luck." I looked at the Japanese, 超高校級の「幸運」, and that's just as good of a direct translation as any, but it doesn't really fall in line with the other titles and it certainly sounds very awkward in English. Granted, "luckster" is a little weird too, but it does at least fall in line with the rest of the students' titles.
English and Japanese are certainly very different languages and certain things in Japanese just do not translate well directly. These kinds of problems require a good deal of thought and sometimes a little bit of luck to come up with something that sounds really nice.
