Yes. Translators lacking the necessary context is a hard problem in general, regardless of the base language or dialect. Mappers like @maro21 have added a lot of helpful contextual hints in Translatewiki.net, but we’ll always have to be vigilant about issues like landuse=mine being translated as the first-person singular pronoun “mine”.
That said, enough open source projects use American English as a development language that most translators and their tools assume this dialect. For example, in Translatewiki.net and any other modern translation management system, one of the main translation aids is machine translation results from Google, DeepL, or the like.[1] These services are configured to assume American English, and I’m unsure if there’s any way to change that to British English, let alone some concept of OSM English that no translation service supports as a source language. Translators are supposed to double-check that the suggested translation matches the contextual hint or rely on their familiarity with the software, but unfortunately not everyone exercises that level of care.
On the bright side, Translatewiki.net also shows translators the equivalent translation in another language they speak. So ideally getting a translation right in one language will give translators in other languages a heads-up that they need to take the machine translations with a grain of salt.
The absence of this functionality is one of the main complaints about JOSM’s translation setup. ↩︎