Let's start with translations. The Walter Kaufmann and Kaufmann/R.J. Hollingdale translations are still the most widely available, and they are generally fine. Kaufmann tends to sacrifice literalism in order to capture the "feel" of the German prose, and he does so well and better than most translators. (This makes his translations a bit problematic for scholars, but preferable for those new to Nietzsche.) Hollingdale's solo translations tend to be rather flat-footed, or so it seems to me. Cambridge University Press has been releasing new translations of many of Nietzsche's works, and these are generally pretty good, though I see no reason to prefer them to the Kaufmann translations. There are other translations around, of which the Clark and Swensen translation of On the Genealogy of Morality is probably most notable.
I am a college student out in California and I found your name among many Nietzsche blogs and thought you would be a good source for insight. Many of
my friends have got me very interested in reading Nietzsche but I feel overwhelmed
when deciding where to begin. Could you possibly give me your insight to what I
should read first and who offers the best translations? Thanks so much.
What to read first? The very first thing I read by Nietzsche was the excerpt from "On Truth and Lie in an Extra-Moral Sense" in Kaufmann's edition of The Portable Nietzsche. I was hooked, though as it turns out that little excerpt is not especially representative of Nietzsche's philosophy. A better place to start might be with Beyond Good and Evil, especially the Preface, and Chapters 1 ("On the Prejudices of Philosophers"), 5 ("Natural History of Morals") and 9 ("What is Noble?") (though the whole book is worth reading). That might be followed by Nietzsche's On the Genealogy of Morality, which could be read in conjunction with the chapters of my Nietzsche on Morality discussing each essay.
From there one might go in two directions: backwards to The Gay Science, one of Nietzsche's earlier works, or forward to The Twilight of the Idols. I'd probably recommend the latter: this is a late work, not as overwrought as The Antichrist or Ecce Homo, but philosophically substantial, covering most of Nietzsche's main concerns.
There are two fine biographies of Nietzsche in English: Ronald Hayman's Nietzsche and Rudiger Safranski's Nietzsche: A Philosophical Biography. The latter has the virtue of giving capsule summaries of the themes of each of Nietzsche's books. The summaries aren't bad, though Safranski's philosophical understanding and competence is clearly very limited. But as a place to begin, it is useful, and the narration of Nietzsche's life is interesting.
I don't think there is a reliable and genuinely introductory book on Nietzsche in English. Michael Tanner's Nietzsche, which some people I respect do like, always struck me as neither accurate nor philosophically competent. Kaufmann's old Nietzsche: Philosopher, Psychologist, Antichrist is extremely unreliable, and should be avoided. George Morgan's old What Nietzsche Means may, in some ways, be the best single volume introduction--though perhaps with too much quotation and paraphrase, compared to exposition. If you have some background in philosophy, Chapters 1-4 of my Nietzsche on Morality will introduce you to Nietzsche's moral philosophy.
I'd be curious to hear from readers where they started with Nietzsche, and what they would recommend to someone new to his work.