知る vs 分かる perspective
I find myself having to ‘think about which of the many meanings is being used’ and that slows me down and causes headache it.
I see this phenomenon often and while unfortunately I don’t know what might help specifically, one thing that I always like to bring up is the fact that for these words often there aren’t “multiple meanings” but it’s more like there’s “multiple ways to translate them” (based on context) into English. A lot of times (admittedly, not always), there is no clear cut “which meaning is it?” kind of question with a clear answer, and worrying about that is just going to muddy up your understanding of the language and its nuance.
Try to think of it from the opposite point of view. Imagine you’re a Japanese person reading an English sentence. As you know 分かる and 知る can both mean “to know”. Imagine you’re Japanese and see this sentence: “I don’t know him at all”. And then you ask “What meaning is used for ‘know’ here? Is it 知る or 分かる?”
The answer is… it’s neither. Or at least, it doesn’t matter. The word is “know” because we use “know” in that sentence in English.
Maybe this gives you a better understanding what I’m talking about, but generally speaking, in a lot of words in Japanese you have these multiple meanings but they really all mean the same thing. You need to try and internalize all those meanings into a general understanding of what the word represents, and for each of us I feel that’s a different thing. Some people imagine a scene in their head. Some a picture. Some a sound, a color, an emotion, etc. All I know for sure is that no matter how much time you spend on a dictionary (either J-E or even J-J), you will never “get” the word and its internalized meaning until you actually spend enough time with the real language to get a more thorough personal understanding of it. That’s the moment where you really stop translating and just let the words create scenes in your mind. It happens at different times for different people, maybe someone smarter than me can give you more useful tips, sorry.