Personally, I think it is definitely best to read the series in order the first time through. One of the chief attractions, I think, is to see how the Legendarium evolved over time. You definitely miss something in this regard if you start in the middle. I realize of course that many people don't want to do this, which is fine; nonetheless, I think they're missing something. Then again, I'm one of those people that really enjoys the extensive commentary and copious notes; in fact, I rather wish Christopher Tolkien had provided more extensive commentary in some places. So I suppose I'm somewhat atypical.
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