That was one of the little extras I was looking forward to in my car.
I first started with a PNY 4GB Flash drive, and I had much the same trouble. I found it annouying to load songs on to it, and then more annouying to get it to play them, I eventually found the best way (as elp_jp said) was to just use Windows Explorer and dump all the songs into the main folder on the drive. BUT after a few weeks I noticed even on "Random" it still only cycled thru about the same 30 songs on the flash drive, which really annouyed me.
I eventually went and bought a new iPod Nano (4th gen) just for use in the car and it works a LOT better. The biggest difference right off the bat is that when you hit Next Track, it instantly changes to the next song with the iPod, where as the Flash Drive took up 30secs to change songs and for the read out on the iDrive to change. On top of that it's a LOT easier to get songs on there and even playlist and the sound quality is a lot better than the Flash drive too. The only odd thing about the iPod Nano was I had to turn on the "Shuffle" option on the iPod itself in order for the "Random" function to work in the car.
I know it's a bit more, but if you really want to listen to your own stuff in the car and half the option, I highly recommend getting/using an iPod. Plus if you order online you can get the free cool engraving I got!
http://www.m3post.com/forums/showthread.php?t=238532
Oh, not to jack the thread, but one thing I've noticed recently. . . my iPhone was almost dead so I hooked it up on the way home to charge it, and while listening to songs, I noticed that they sounded even clearer (and the bass was more pronouced) with my iPhone over the iPod Nano, not sure if anyone has experimented with this or noticed that, I wonder if a bigger iPod would produce better sound?
Quote:
Originally Posted by SenorFunkyPants
I use a mix of folders and single tracks on my USB drive and idrive recognisies them all.
Secondary question: If you select "Random" play for the USB drive music, does "Random" remain selected after you switch the car off and then on again later?
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Yeah, it saves the Random option when you turn off the car. It usually only forgets it when you unplug the device from the car and plug it back in.