Cristobal,
Thank you for this; I knew that Google didn't work so well for all language pairs (there are a lot of them, apparently, where it starts by translating them from the soure language to English, and from English to the target langauge), but I thought the English/Spanish pair was sound. It's sad to hear that it's asymmetrical.
I'm planning two or three follow-up pieces to this. One of them is a serious consideration of the limitations and their consequences, and of how the effects of Google Translate may play out, in general. Your take on this, then, has been greatly helpful, as it gives me a good place to start a discussion of asymmetry.
On that note, I have a question; would Spanish translate well to another language that didn't require context in the same way English does? I'm unfamiliar with other languages but say we were going from Spanish to Portugese, which I know is a fellow romance language to Spanish (and the dominant language of Brazil, which is apparently the largest user of Google Translate). Would your example, “debería ir,” translate cleanly if the two languages had similar rules about what does/does not require context?
One idea I'm exploring is that in a world where computers could easily mediate translation, we might still wind up with linguistic divides simply because some translation pairs don't work well and so even with a computer translating communication is still choppy.