My iPod stays in my car, connected to my head unit's USB adapter. It really is quite convenient for that purpose. All my CD's are ripped using Apple Lossless and then I use my older version of iTunes to convert that to the highest quality lossy AAC format to fit on my iPod. I have to drive a lot, so it is a blessing when I can avoid the banal music of the local radio stations. (I hate pop music, it all sounds the same even if it is on a rock station, "alternative" rock station, or country station. Now the only difference between pop and country is a fiddle and a southern accent.)
But I've been seeing the writing on the wall for a little bit and started looking for alternatives. I know about Fiio. I also found out Pioneer has a program where you can transfer your music and playlists from iTunes to a program they have. And then that program can be used to put your music and playlist on a SD card or USB drive for Pioneer units. iTunes version 10 and earlier are great at organizing music; version 11 and later is garbage at everything. I found my alternative. I don't have to redo my playlists, I don't need to re-rip my music. And since I like Pioneer head units, I stopped looking.