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If I am assuming correctly by your post that this is your first Rolex, buy a well-preserved (recently-serviced, if possible) specimen that is a few years old. Save some money by purchasing WELL below retail, wear it, love it, and as you do, figure out if there is anything about it that you don't like. By that time, you will have fallen in love with the watch (and you won't care), or if not, you will be able to re-sell it without losing a dime.
Such will not be the case if you buy new.
Figure out the look, feel, and features that you want, and the list of candidate watches should be pretty short.
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