Given a source language and a destination language, I wonder if a linguist could design a series of translations that exacerbate the loss of meaning which occur

Given a source language and a destination language, I wonder if a linguist could design a series of translations that exacerbate the loss of meaning which occurs when words are automatically translated from the context of one language to another. When I write something that I intend to automatically translate, or that I know will likely be read in translation, I often use a simple reflexive translation from source through destination and back to source in order to detect any lack of clarity in my words. Seeing a smoother, more automated feedback while writing for translation would help people improve their communications.