There are several things to keep in mind. 1) what I think sounds good you won't necessarily agree with. (I strongly dislike Bose speakers, they are too muddy to me. My wife, however, thinks Bose is the bees knees.) 2) what music you play and the quality of the rip will play a big role in determining the quality of the speakers you need. I listen to lots of jazz and instrumental music which is ripped at a very high quality level. My brother listens to uh, the stuff played on MTV, and he rips his files so he can fit lots of them on a 4GB iPod. Whether he spends $10 or $100 on his speakers won't matter in the least 🙂 3) the room will have a big influence. I had a set of Harmon Kardon speakers that sounded great in my basement office but after I remodeled it, without the cement floor and walls to bounce the sound off, the speakers sounded tinny and one dimensional. Thankfully we hadn't yet wired the den because I wound up running an audio out from my computer to the den stereo system and adding a pair of speakers for my office.