This was posted in another thread recently and I agree with most of it
https://dl.dropboxusercontent.com/u/10804397/1438025480037.png
As far as headphones are concerned there is a lot of variety to choose from, you should do some research and decide on priorities (things such as open vs closed headphones, soundstage, mids, warmth, neutrality, etc.). Headfi is a good site to use as reference.