The problem with translating any Chinese classics lays in their multi-layered meaning. Old Chinese literature is complicated because every author expected that the reader was accustomed to volumes of other classics and could comprehend all the references to them hidden in the text. No matter how many good translations we have, they will not help us resolve this issue. Furthermore, understanding Dao De Jing is problematic even for native speakers of Chinese, because they do not have proper educational background to comprehend what ideas the author wanted to convey even being able (as they think) to read the original text!
> The problem with translating any Chinese classics lays in their multi-layered meaning. Old Chinese literature is complicated
I concede that can be troublesome. But, from a different perspective, it’s also kind of liberating.
> understanding Dao De Jing is problematic even for native speakers of Chinese
That being true, it allows you enough room of not being ashamed of your own interpretations, if you find them useful. In that sense, the text is much more alive, talking to you directly, instead of being an unsolvable puzzle that takes you away from it.