I have a pair of Grado SR-60 headphones, and I have no complaints. In your price range (which was my price range too) I don't think you can do any better than the entry-level Grado products. I suggest that you check out headfi.org and headwize.com - they are dedicated to all things headphone.
I can't help you much with the amp. I recently purchased an older Rega Ear, but I have only a couple of hours of time on it thus far. Hope this helps.
I can't help you much with the amp. I recently purchased an older Rega Ear, but I have only a couple of hours of time on it thus far. Hope this helps.