I've been working on a new bentcher (birkon, for the purists), hoping for it to be ready by my son's Bar Mitzvah. The goal is to produce a text which is easy to read, and which includes English translation as well as transliteration and commentary for the songs of the Shabbos table. I'm not aware of another bentcher which includes all of these elements.
For the transliteration, I'm largely using the work of the "Yale Bentcher". For the translation and commentary, though, I'm starting from scratch.
In the process of doing this, I've encountered quite a few places in which the translator must make the choice of following different commentaries. For example, the phrase in Kiddush, "כי הוא יום תחלה למקראי קדש זכר ליציאת מצרים," associating Shabbos with the commemoration of the exodus, admits of multiple explanations.
Another challenge is whether to translate songs in ways which highlight their puns. For example, Yom Zeh Mechubad includes the line, "על שתי לחם יבצעו תמימים," which has a double meaning - "upon two unblemished loaves of bread they will slice", or "upon two loaves of bread, the unblemished nation will slice". The former, literal approach is the one I've seen in various translations, but I favor the latter.
And another challenge involves translating phrases which may have been shifted from their proper grammar for the sake of rhyme or meter. One is the phrase ולנוח בחבת in Mah Yedidus; another is נעים שמכם in Dror Yikra. The standard translations take them entirely non-grammatically. For the former, I think a proper translation can work if one reads this as part of ולנוח בחבת כשושנים סוגה, which does fit the sort of enjambment seen elsewhere in the song. For the latter, I'm genuinely stuck.
It's an interesting process. Stay tuned!