I have 0 confidence that I could understand the Tao even if I read the best most classical translations available.

Take the bible, which is translated from languages that are closer to mine, and which refers to a culture which is closer to mine, with family and scholars whose interpretation I can understand directly. Still I don't have much confidence that I understand the bulk of it, it takes years of reading and lived experiences to understand both the modern and past contexts in which it was written.

By the same token, I'm certain actual chinese people read the Tao and are like "Lmao what does this mean", and for the most part these books are meant to be mysterious, iirc there's actual sections of the Tao that translate to "You can't understand the Tao".

I don't mean to be overly religious here, it's just that the Tao happens to be religious, but consider Beowulf, which is written in an old form of the English language, surely you would be able to understand it? Not a chance, try it. But ok, surely the translators are able to understand it and provide you a translation without losing much meaning. No, not only can they not provide a translation that you can understand without losing context and signal, but they can't understand a lot of what they are reading anyways. Consider that for just the first word of the whole epic, they are still fighting over what 'Hwaet' means, nobody can even settle on what the first word means! Imagine the rest of the text.

So to think that one has a chance to understand the Tao, or even that it is worth it at all to understand something from a culture so different. Not for me.

Unless you are Asian, by all means go for it, but if you are not, I would invite you to question whether you first have any chance at understanding at all, or whether you will interpret "being like a Straw Dog" from whatever translation you chose through your own lens, like a Rorschach.

This seems overly pessimistic. We regularly engage with other cultures and their texts and understand them, and, yes, it takes time and knowledge of context to do so. Someone needs to explain quite a bit about Roman society under Augustus for you to understand what is going on in detail in Ovid's Amores, and the Epic of Gilgamesh is pretty bizarre unless you know quite a bit about ancient Mesopotamia. The Tao te Ching suffers from being written in a style that was very much for people in the know in a certain milieu, limited texts, and a huge amount of cultural baggage on top. The most interesting recent scholarly translation I know of is by Victor Mair, of a different, recently discovered text, and his contention is that the book is a 'mirror for princes' and not a mystical text at all.

> they are still fighting over what 'Hwaet' means

I don't think anyone is particularly fighting over what it means, just how to translate it when there isn't a parallel in modern English. My personal favorite is a translation that opens with 'Bro!'.