Sources and translations
Here is a (non-exhaustive) list of resources I use when prepping CRTTC:
The best place to start:
Tasuki.org - probably the best possible resource for understanding the subtlety and nuance of the text. Here you can access 11 different translations and pick and choose to compare them side-by-side. This link opens five that I use most often, but I also use a number of the others from this site as well.
Translations and paraphrases
Marshall Davis's The Tao of Christ - an amazing translation that adapts the TTC language into Christian terminology, doing some minor modifications where needed. Mr. Davis is a rural pastor from my own home state of New Hampshire, and he's written a number of books which I deeply admire!
R. Joseph Owles' Everyone's Tao te Ching - this is one of my favorites! It's an absolutely beautiful translation with some pretty heavy paraphrasing at times. I can't recommend this one highly enough! I think it would be a great starter if you want an accessible, easy to read version of the TTC.
Tao te Ching (new translation) - for a mere $3 on Kindle, this new translation is a steal. Although the authors are not Chinese scholars, they have read numerous translations and synthesized them into something that feels really fresh. They take some liberties in paraphrasing, but when they do, it is usually insightful. Highly recommend.
David Jones's The Way and the Word: The Tao of Jesus - this brilliant and totally unique little book is part paraphrase and part improvisation. Jones follows the 81 chapter structure of the TTC, but he often paraphrases heavily in his translation, and then feels free to add lines from Scripture or Christian thought to really round out each chapter. It is beautiful, and probably my favorite source of all of these, but it doesn't actually qualify as a "translation."
For studying the original text
Tao te Ching: The Definitive Edition - this book deserves its title. It has every single chapter, character by character, with a long list of the possible word-for-word and paraphrase-worthy definitions of each character. I've heard it described as a "choose your own adventure" translation, where you can study each character and choose the phrasing that you like. The author also includes his own translation, which is equally brilliant. A must have for any serious student of the TTC.
The Way and its Power - an excellent site that includes the TTC in its original text, where you can mouse over the Chinese characters and see their literal meaning. It also has a few literal translations and some commentaries in multiple languages.
Commentaries and other resources
Hieromonk Damascene's Christ the Eternal Tao - also not a translation, but an amazing (although somewhat academic) book exploring the history of Taoist thought and the profound parallels with Eastern Orthodox Christianity throughout the centuries. Damascene also has written a series of 9 "enneads" that are sort of a "new," Christian Tao te Ching. This book is a gem.
CenterTao.org - an almost overwhelming wealth of knowledge. This site contains decades of blog posts from Carl Abbott, a quirky genius who has been blogging through the TTC chapter by chapter for years, doing his own translation work and then revising and commenting on it each time he comes back around to the same chapter. There are also tons and tons of lengthy essays on spirituality and Taoist thought.
The Tao te Ching Explained - Stefan Stenudd has his own translation with brief commentaries on every chapter here. He also has a wealth of other resources, TTC-related and otherwise.