Advice for Newcomers (With a Twist?)

Reader Oscar writes to me:

I'm a Spanish reader, and I'm very interested in Shakespeare, but I'm a newcomer. I've just read only some works by Shakespeare, but my purpose for 2013 (in reading terms) is to deepen in the Master's works. I'd like some guide about it, I mean, what are the works I must begin with, the most difficult ones, etc. Could you help me? I'd thank you so much...

Although I told him that we'd discuss it here, I did ask a few questions, at least one of which I think puts an important twist on the question:

1. As a Spanish reader, does that mean that Oscar is reading the plays in English, or in a Spanish translation?  Does that change your answer?  Are there some plays that might be altered in translation more strongly than others?  What happens to the more "poetic" of the plays?
2. What is the reader's interest in the life and times of Shakespeare, and Elizabethan history in general?  The works take on a different level when you look at them in context of what was happening around Shakespeare at the time.  Which plays are more timeless, and which really require an understanding of Shakespeare's time to fully appreciate?

In writing back I suggested Much Ado About Nothing.  High quality romance, one of Shakespeare's best couples.  Easy plot to follow.  Not too many lengthy poetic passages to deal with in translation.

So with all that in mind, let's discuss.  Where should the newcomer start?