On this topic, Douglas Hofstadter's book Le ton beau de Marot is organized around this and related topics: poertry, translation, language and literary play, and the challenges and freedoms offered translators, all woven in typical Hofstadterian fashion with a breathtaking array of topics and observations. One of my favorite books, and it may interest anyone who, as you say, is fascinated by translation and its difficulties!
Fair warning: the book gets a bit dark in parts (he wrote it after his wife's death, and covers that a bit), but not overwhelmingly or throughout.
ETA: To address your original question, Hofstadter's book is organized around the challenge of translating "Ma mignonne", a very tight little French poem by Clément Marot (hence the book title), and goes into great detail about the challenges it presents, with lots of different approaches and translations. He talks about many other significant challenges to the translator -- the one that comes to mind is La disparition by Georges Perec[1] -- a novel famously written without appearance of the letter e. It was translated into English by Gilbert Adair as A Void -- also lacking that most common of glyphs. Other unpublished e-less translations exist, as well.
Fair warning: the book gets a bit dark in parts (he wrote it after his wife's death, and covers that a bit), but not overwhelmingly or throughout.
ETA: To address your original question, Hofstadter's book is organized around the challenge of translating "Ma mignonne", a very tight little French poem by Clément Marot (hence the book title), and goes into great detail about the challenges it presents, with lots of different approaches and translations. He talks about many other significant challenges to the translator -- the one that comes to mind is La disparition by Georges Perec[1] -- a novel famously written without appearance of the letter e. It was translated into English by Gilbert Adair as A Void -- also lacking that most common of glyphs. Other unpublished e-less translations exist, as well.
[1] https://en.wikipedia.org/wiki/A_Void