I'd just start reading In the Buddha's Words (that's what I did...). The first chapter is available as a PDF here: http://wisdompubs.org/Pages/display.lasso?-KeyValue=104
in the link: "A PDF file of the table of contents and other frontmatter".
There is a series of talks based on the book here: http://www.noblepath.org/audio.html
(scroll down to the bottom section).
Bhikkhu Bodhi has organised a selection of suttas in a classification scheme that I found very helpful.
Bhikkhu Bodhi wrote:In an ongoing series of lectures I began giving at Bodhi Monastery
in New Jersey in January 2003, I devised a scheme of my own to organize
the contents of the Majjhima Nik›ya. This scheme unfolds the
Buddha’s message progressively, from the simple to the difficult, from
the elementary to the profound. Upon reflection, I saw that this scheme
could be applied not only to the Majjhima Nik›ya, but to the four
Nik›yas as a whole. The present book organizes suttas selected from all
four Nik›yas within this thematic and progressive framework.
I have found what he says here to be very true:
Bhikkhu Bodhi wrote:Once one understands the scheme in this book, one should come away with
a clear idea of the architecture of the teaching. Then, with a little
reflection, one should be able to determine the place any sutta occupies
in the edifice of the Dhamma, whether or not it has been included
in this anthology.