I grew up leaning, reading and davening with a "Havara Ashkenazis", which was and still is the norm in many communities in North America. The poskim seem to be in favor of sticking with the same pronunciation that was learned from one's parents, teachers and community (see Iggrot Moshe O.C. 3:5). Today, we really have no idea what the correct system of pronunciation is, and therefore it is probably best to stick to the minhag with which you were raised.
It is for this reason that I continue to read, learn and daven as I did when I was a young child and this has also been my usual preference when writing Divrei Torah in English.
I think that for the purposes of this blog, I will make the jump to transliterating the Hebrew words and phrases with havara Sefraradit ("Shabbat" for example, as opposed to "Shabbos"). I think this will just keep things clearer in the long run... (in any event, the whole discussion about preferred pronunciation seems to apply only to actual speech and not to the written word - see the examples quoted by R' Moshe in the teshuva I mentioned above).
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