For your problem there is a simple solution:
Assuming all your music is high resolution, such as Apple lossless, this will not play from a USB thumbdrive in most cards. Here is how to accomplish your goal:
Create a NEW library in itunes.
(option open iTunes to create a new library)
Import all the music you want to have available in the car.
Set the import settings to .mp3, custom settings, 320K (for best fidelity)
Select all the music in your library
From the File menu: Convert: Create Mp3 version. (this will convert all your music in your library. - it will take a while)
When completed, sort by kind and delete all the lossless music, keep only the MP3.
Now you have a library with only car music!
Start with any USB Thumbdrive. It must be MSDOS formatted.
Manually copy your .mp3 files onto it.
(They can be in folders, such as by album name, etc. There are limits, but unless you are really loading up large Thumbdrives, you are unlikely to hit it, so leave your music sorted as in iTunes folders.)
The next step takes some command line steps, but is not hard to figure out.
Name your Thumbdrive a short name, no spaces, such as MUSIC
Now when you have the Thumbdrive ready to go:
Open the terminal.app (Utilities folder)
Paste the next two lines in: (change MUSIC to your name of your Thumbdrive volume)
cd /Volumes/MUSIC
find . -name ‘*.DS_Store’ -type f -delete
When the process is completed, you will get a command line prompt.
Quit Terminal.
Unmount your Thumbdrive
Put it in your Car USB port, and when it shows up, you can sort by name/artist, or play randomly.