It helps if you just bite the bullet and realize that you're going to pay a dollar a song for infinately portable, high quality music. I gave in a few years ago (hard to believe it's been that long) and I've amassed a pretty good collection. My music is mostly on Vinyl (I have enough LP's to break my oak book shelf in multiple locations) but I have amassed a pretty big number of songs over the last few years.

If you can't read it it says 4 days, 1300 or so songs. The trick is to buy bricks of stuff you know you want to listen to. Instead of searching for specific albums, try to use the Itunes Essentials in the lower left corner as they're groups of about 75 songs that you can pick from individually. An Itunes Essentials "pack" consists of "the basics" (songs everyone knows) "The Next Steps" (songs most people know) and "Deep Cuts" (songs you probably havent heard.) You can pick and choose from there. The "packs" are unified around a central theme like "Eric Clapton" or "The Sixties."