Literally all the time. I just translated a short paragraph:
In these few lines, we have brahmā, which shades in meaning from the supreme deity of Brahmanism to simply “highest, best” to “holy”. Kāya means “body”, but also moves towards the sense of “company, collection, corpus”. Dhamma most commonly means “teaching”, but has a range of meanings, which here shades off into “truth”. You’ll notice that in some of the passages in that post I have translated Dhamma as “teaching”, in others “truth”: I haven’t decided if I will keep this difference, or make them the same, and if so, which one.
These are three important words, and in this one passage they all have such an ambiguous meaning that it is not easy to decide.
Like i said, this is neither a bug nor a feature, but the fundamental principle in how language works. We do this kind of thing constantly in our own languages, but we are so used to it that we don’t even notice. It’s only when we are learning another language, we get stuck on literal meanings and don’t yet have an intuitive sense for the ebb and flow of natural sense. Over time, you get a feel for it and it becomes second nature.
I really don’t think so. As far as I’m aware, the dispute about the interpretation of vitakka/vicara has only arisen in modern times, and mainly among people who don’t know Pali very well. I’m not aware of it being controversial in ancient times. As far as I can see, it’s just a side-issue that’s arisen in the wake of the vipassana school, who created a huge amount of confusion around the whole topic.