As someone knee-fucking-deep in Intermediate hell, I am well acquainted with it's despairs, which no doubt appear frivolous to a beginner who's still mired in the base and heavy despair of doubting whether he can succeed, but are yet still heavy and wearing on the soul. The first and greatest despair is what I've come to consider "situational" or "limited" fluency - someone in Intermediate Hell is very likely competent to fluency levels on basic grammar, understanding everything, for instance, in a moege with little to no problem, but being completely unable to read a news article or even a brief anecdote on unfamiliar territory such as fishing or mathematics. It's heavy despair to be so competent in some areas and is incompetent in others, it makes you doubt yourself and your proficiency. The second greatest despair is the simple weight of unknown vocabulary, the wall of unknown words you hit, the just plain obscure or difficult vocabulary that's not jargon, but are just normal words any author may use if they know them (http://pastebin.com/vdqDgLdV
); this hits hard simply due to their large bulk of tens and thousands. The third greatest despair is the "Nimrod phenomenon", which is encountering language that not even a native would properly understand, embodied in Bugs Bunny's usage of the word "nimrod" which not even natives understood. You can be reading a book and come across something you just plain don't understand, only to learn that natives struggled just as much to understand. This is despair because it reminds you that even at native-level you still have a lot to learn.
Compared to struggling with Yotsuba, the despairs of intermediate hell are perhaps not as frightening or weighty, but they do exist and they do hit hard.