Can one make a rule about translating a particular root? Let's start this in an easy way - with just a few words.
nephesh - literal meaning throat, typical 16th century translation, soul, - what is it? the "I" in me, my life, my being, my inmost-being, myself, my self? It is pervasive and common in the text that we have.
shalom - peace, well-being, wholeness, soundness, welfare, completeness
yara - fear, reverence, terror
chesed - lovingkindness, mercy, rebuke, covenant love
I don't think I can make a rule for any of these. If I did, I would be stuck. Take the first two: our presenter presented a slide with nephesh as inmost being and shalom as well-being.
Problems: immediately there is a false sounds-like connection between the two words. [but there is an assonance in the Hebrew! - did it take you 4 years to figure this out?] [Yes - but equally] I would have to translate the first occurrence of shalom in the Bible as "you will go to your grave in well-being" - sorry - that's not going to work. [too many syllables :)] While concordance (same gloss in English for the same lexical word in Hebrew) is more often than not desirable, it is desirable only within limits: where the sound is repeated for effect, and where some degree of intertextual reference is intended. Otherwise, the translator is free to find the gloss suitable to the context.
What about fear - reverence - terror. In Job, there is a stanza that has differing words for fear in the Hebrew - so we must find differing words for it in English (see my post here.) And fear of Hashem is a legitimate start to wisdom - it is not reverence but fear - for this is not a tame lion.
What about chesed? Suppose you made the decision to transliterate and not find an English gloss? You would be stuck - how would you deal with chasid the adjective as applied to God, or how would you deal with chasidim, the plural as applied to the targets of God's chesed? I think when our language is defective, we may need to coin a word. So if chesed is mercy, chasid is merciful and chasidim are the mercied - the ones who are the target of the loving kindness mediated in covenant with Hashem. (now that's a mouthful).
I have noted already that chasidim are the plural counterpart in the psalms to the singular unidentified ish (man / woman / person) in verse 1 of psalm 1. The singular turns to plural - one righteous produces much fruit - the produce of the earth, the vine of Israel.
Four more considerations:
Can one transliterate sometimes? I think so - but I did it only with the word for the tetragrammeton (YHWH) and I preferred to leave it in the Hebrew characters - a thought that I gleaned from John Hobbins of Ancient Hebrew Poetry. Doing this saves a lot of grief in English since a Name behaves better grammatically than a Noun.
Now what about gender inclusiveness. When the host language is defective, it must be changed. Or one must have a disclaimer. English is defective politically. So sometimes I use human instead of man, and earthling or child of dust or the like and sometimes I use 'it' and 'its' for third person common pronouns - works very well in Qohelet especially in the style of Dr Seuss.
In so many ways, I am indebted to the folk at BBB (you know I don't believe in better) and to Kurk Gayle at Mind your Language and to Joel Hoffman at God Didn't Say That - because they have all sorts of commenters who talk about these questions so I don't have to - I can just do it. Kurk has more fun than the lot of them put together.