One thing I used to narrow down a few translations for deeper reading is to understand the author's background, because each of them bring their own flavor to the text. For example, based on the three I have handy -
John C. Wu - chose it because of his background in Law and Policy (things I'm into), and his history with other religions and religious texts (ie, Christianity).
Red Pine - being a westerner that transitioned reasonably far into Chinese language and culture, and his involvement in Taoism as a religion
William Scott Wilson - because of his extensive work with translating Japanese texts and exposure to Zen / Bushido, and the flavor it brings to his translation
This may be a dud metric to assess texts but I find each brings elements of the author's experiences with them in the conversion process.
Found Wing-tsit Chan's translation a very nice read as well. Red Pine's is a lot of fun too, it's very rough and abrupt (in a good way).