I guess it really depends on how familiar you are with the night sky - but there's one book that's literally invaluable for astronomers of all levels - Turn Left At Orion - there's no finer book, quite frankly, and the authors are an inspiration to me. If my books were anywhere near as good as theirs, I'd be very pleased and proud.
(Get the larger, spiral bound edition - http://www.amazon.com/Turn-Left-Orion-Hundreds-Telescope/dp/0521153972/ref=sr_1_1?ie=UTF8&qid=1414368749&sr=8-1&keywords=turn+left+at+orion)
I would also buy Astronomy Hacks - there are a TON of tips and tricks in there and, again, it's aimed at astronomers of all levels.
I had an Orion XT 4.5" Dobsonian and loved it. Celestrons are also excellent and both companies have equipment that are reasonably priced and well suited to amateurs of all levels. I'd start with something relatively small, like a 4" or 6" reflector and then go from there.
Beyond that, I would highly recommend joining a local club or, at the very least, ask a question here on Reddit or join a group in Facebook.
The two I like the most are the Telescope Addicts (https://www.facebook.com/groups/telescopeaddicts/) and Astronomy 4 Beginners. (https://www.facebook.com/groups/astro4beginners/)
I hope this helps. Feel free to email me at astronomywriter@gmail.com at any time. At some point in the nearish future I'd like to write an astronomy book for suburban astronomers (especially beginners) but I'm not sure when that might happen!
(In the meantime, have a look at my other book, 2015 An Astronomical Year - the Kindle version has a lot of graphics and text highlighting the best naked eye sights throughout the year - http://www.amazon.com/dp/B00LVEUJI2/)
Clear skies!