I've been leading a book study once a week on the Sutta Nipata. This is a challenging and fascinating exercise. So I'll share a few general thoughts about reading suttas and post links to some helpful resources.
Why read the suttas? There are hundreds of Buddhist books out there; good, bad and middling. Many western Buddhists have read dozens of them without cracking the scriptures. This is a shame; you want to get the straight goods, you should go directly to the source. The whole sutta pitaka has now been translated, parts of it several times. If you want to have a firm grasp of what the actual historical Buddha taught, as opposed to all the various re-castings, spins and speculations, why not check out his own words? This is especially important because so many people have put their own words into his mouth over the centuries, as discussed by my post Check Your Sources.
How to Read the Suttas. First remember that they were originally oral literature. So don't be put off by all the repetetions and numbered lists; these were aids to memorization. They definitely have a deeper resonance by being heard rather than read and some people like to read them out loud. Some of the beauty of the language is lost in translation; large portions like most of the Sutta Nipata are actually verse although the translations tend to be in a rather dry prose. Stylistically, the suttas are a very rich and diverse collection. There are straight technical sections, devotional passages, myths and stories all intermixed.
Problems of Translation. Never forget that languages are not completely isomorphic. Even the best translation is not completely true to the original, it cannot be. Even if you go to the effort of learning some Pali, you can't escape the problem entirely (although it helps.) It is however important not to become overly reliant on the bare English words which often translate Pali words inexactly. This is not sloppy translation; it is an insoluble problem because some words in Pali have no exact English equivalent. Pali has a very precise technical language for mental states and spiritual phenomena, something which English lacks. To give the most obvious example, dukkha is not the same as suffering. One of the best ways to get around this limitation, at least in part, is to acquire a working vocabulary of technical terms in Pali and refer back to them when in doubt. A very good resource here is the Buddhist Dictionary by Nyanatiloka. (Link is to an online version).
Some More on Translations. The best translations available at present are by Bhikkhu Bodhi and his teacher Nyanamoli. Maurice Walshe's edition of the Digha Nikaya is also very good. Many texts are still only available in the Pali Text Society editions dating to the early years of the last century. These works are generally very good from a purely linguistic point-of-view, but often lack the background in the actual living tradition which informs Bh. Bodhi and M. Walshe. Readers should also be aware that some of the PTS translators imposed their own ideas onto the work. A well known example is the way Mrs. Rhys-Davis and to a lesser degree I.B. Horner translated the particle atta. They wanted to "prove" that Buddha never actually taught no-self, so whenever this particle occurs, they take it as a substantive noun. A close analogy would be the use of the suffix -self in English words like myself, yourself, oneself, which does not imply a metaphysical entity. See this article, anatta6, for a discussion.
What to Read. If you are new to the suttas, or even if you're not, the best place to start would be with Bhikkhu Bodhi's In the Buddha's Words, which is a collection of suttas and sections of suttas arranged thematically and progressively together with copious explanatory notes. Another good overall collection is Nyanamoli's Life of the Buddha which arranges all the narrative sections of the suttas into a chronological sequence, together with some sections which relate the most important teachings.
When you are ready to go to the original texts in whole collections, the best place to start is usually with the Digha Nikaya, and then go on to the Majjhima. After that, you can proceed as your interest goes; deeper into the philosophy with the Samyutta for instance, or get the flavour of the myths and stories with the Dhammapada commentary or the Jatakas.
Resources and Aids. Many of the suttas are now available online at accesstoinsight.org. These are mostly in Ajahn Thanisarro's translations. These are quite good, but the novice should be aware that the Ajahn's choice of words is often not standard and this can lead to confusion (example: dukkha is translated as stress)
I've already linked to the indispensible Buddhist Dictionary, another amazing web find is the entire Dictionary of Pali Names, in the hard-cover three fat (and expensive) volumes. This is a real treasure trove of information if you like to dip into the stories behind the names.
Not online, alas, but invaluable nonetheless, is a little booklet from the Buddhist Publication Society called An Analysis of the Pali Canon by Russell Webb which provides handy indices to the various suttas.