Buy CDs.
If there's a 1990 version that you can get used, and a 2004 version that is "re-released"(Note: Not remastered) get the 1990 version.(Loudness wars make newer cds sound worse than older ones)
Anyways. You can rip to Apple Lossless. I'd rather just rip to .wav because storage is extremely cheap nowadays and a 750GB drive is like $300 or something. From there you can put your music on your Ipod in Apple Lossless quite easily.
I say for a second pair of headphones go with Sennheiser HD600s or HD650s. You can get the 650s used for less than the price of the 600s new ($300ish) It depends on what kind of music you're in to.
What's your Ipod like now?
http://www.head-fi.org/forums/
Good luck ever having money again EVER now. [img]/images/graemlins/smile.gif[/img]