I use Win 7 too late after midnight, I use Foobar 2000 to play music downloaded through EasyMule. I hear classical with my Headphone - Philips, Denon, old Pickening. Not too bad. Money is not too significant as a start.
IMHO, get the music(s) that you are interested. Search on Web about the music pieces. Why it is so popular? what it is telling you? Videos are even better -for you can see the artists' expression. Then, you can find how different master musicians play the same piece of music. This is the joy of symphony.
By then, you will care for the soundstage, clarity, timbre, treble and Bass balance for your beloved symphonies..