But even when I try to reach for the lowest hanging fruit (I have searched quite a bit for very low hanging fruits), I still feel as though I’m fucking things up horribly. I don’t know enough of the words in a sentence to make the sentence mean anything, and I immediately resort to translation as a means of making sense of it (which is apparently what this site is entirely against). I don’t know how to retain words, as I don’t know of any method that leads to me actually learning the words instead of learning the answers to questions I’m asked. (For an idea of what I mean, when I reverse the questions & answers in Anki, I find that I can’t answer any of the questions.)

Do you know each of the words in that sentence? Can you understand how they’re being used? Do you know (or at least have a pretty good idea) what the speaker/author was trying to get across when they wrote/said this? If you answered yes, particularly to the last one, then you understand it. Do you have to know each subtle thing about the sentence? (in this sentence there isn’t really any though) Do you have to be able to recall the sentence, or one similar to it, at will? No, not really; however, these things will come with time if you want them.
 
Also, when you start doing sentences, you should start bilingual. During this bilingual phase, you should try to use cards that will help you get a basic understanding of how sentences are structured. This should help when trying to figure out sentences when you go monolingual.
 
If you still can’t figure out a sentence, then you’re not ready for it yet. Look for something easier — low hanging fruit — and learn that for now. If you want, you can come back to that difficult sentence later and it may not be as difficult.