Usualy head units only recognize hard drives up to 32 gb and have to be in fat32 format so you would have to portion a drive X amount of times and store as much as you can in each one. Yes they will show WHATEVER the file name is, so if you download it from the internet and it is like johnmayerunknown32s.mp3 that is what it will show unless you update the info, by right clicking the song and click info and type it all in, I rip all my songs via original cd's so this is not big deal to me. I just use my ipod much better and much easier, itunes dose all the work.
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