Below are links for two not really related topics of note. The first one provides a rather massive chart that can help new readers to the Star Trek "lit-verse" figure out a good starting point and then what order to read from there. It seems intimidating but just pick your favorite type of Trek, go to that column and follow the arrows forward or backwards until hit an interesting sounding title. Then search Amazon.com to learn more about that book. If want self contained and off beat, the New Frontier books are excellent reads. Except for The Original Series, most of the books for the last 5-10 years take place in a post Star Trek movie-verse continuity so it continues the sagas of the TNG, DS9 and Voyager crew, with those characters often crossing over. If interested in that, a good place to start is Star Trek: Destiny which features the origin of the Borg in a war to save what remains of the Federation. The full chart and other details can be found here.
In regards to choosing your favorite Star Trek that covers the series, movies and various book series, i09.com has posted a tongue in cheek "guide" to show what your favorite might say about your personality. That can be found here.