USB Drive, Apple Lossless and Hood Scum Theiving Bastards

So about a week ago, Hood Scum Thieving Rat Bastards broke my passenger window and stole my Pioneer head unit, iPad, Garmin and 160g iPod Classic. Luckily my insurance was able to compensate for the damage and some of the stolen items.

I've since ordered a new head unit, Pioneer Appradio 4, but I'm not planning on replacing the iPod Classic because Apple decided to quit making them and they now retail somewhere around $500. Also the iPod that I did have was buggy and would not play some songs which was beyond annoying.

Most of my music collection is currently ripped from CDs in iTunes in Apple Losseless. My question is, and please forgive me of my ignorance, but what is the best way to transfer my collection to a USB stick and maintain album artwork, and organization? Will the head unit be able to make sense of this or does every album need to be in separate folders, organized by artist? Will albums be arranged by year or alphabetically?

Thanks in advance for any help,
Chuck