Hi Matt and
First up how about you start with the basics and just use your eyes to learn your way around the constellatons. Take it slow - they will always be there. Important though that you at least get to know the brightest stars, as this will help you to hop around the constellations. Know where north, south, east and west are too (of course). I bet in time you will form a personal bond with the sky and upon their seasonal return jump for joy in welcoming them back (okay, I do anyway

)
Okay, so Let's go shopping!

1) A planisphere (around $15 from Bintel, Andrews etc) is a must. It will tell you where the constellations are at any given time and month. Priceless as a learning tool.
2) A couple of basic books...
"A Walk Through The Southern Sky" (by Milton D. Heifetz & Will Tirion), will teach you how find constellations, explain the very interesting mythology behinds them, teach you how to measure distances in the sky, lists of bright stars to help navigate you, etc. It's a very simple and easy to understand book - very important when first starting out. Both Liz and I own and love this book.
http://bookdepository.co.uk/book/978...e-Southern-Sky
You can also google preview the book on this link.
"The Practical Astronomer" (by Will Gater & Anton Vamplew) is another great introductory book. Full of maps showing objects and accompanied by lots of coloured pics. Covers all the basic to get you started, and then lots to look for and keep you entertained.
http://www.bookdepository.co.uk/book/9781405356206/The-Practical-Astronomer
I have seen this book at Borders Books for around $30.
Just a note: Some books may have the maps upside down due to northerly orientation, just turn maps around to suit.
3) Dark adapt your eyes for a good 15 minutes - it will help pop out those fainter stars.
4) Spend a lot of time reading through the brilliant tips in this forum. In particular, the two beginner sections (beginner talk & beginner equipment). Trawl through astronomy books & media section as well - there are loads of recommended books. So, read, read, read. I can't stress that enough. When it comes time to get your scope, you will have much knowledge under your belt, to know what you want in a scope etc.
Enjoy Matt!
Kind regards,
Suzy.