iTunes will automatically search the web for album cover art, and then "attach" it to the folder containing that album. It's neat to have, but on the bike I've found that it's not as big a deal having the artwork as it is having it at the house. You just don't have time to check the art out on a bike.
There are other key items to remember:
First, format your USB stick or SD card to FAT32 so it will be recognized by the boom box. This isn't an option. If you don't know how to do this, do the research on line. This may sound harsh, but a little legwork on your part learning how to search for help on line will go a long way as you learn all about this new technology, and there are a lot of websites that offer help in plain english for folks of all levels of knowledge.
Second, it's better to have your music arranged by artist, then albums, then songs. iTunes does this automatically for you. In other words, in the root directory of your stick or card (the first level of storage), you should have nothing but folders, one for your music groups. If you look in one of those folders, you would then see the various albums you have for that group. Then lastly, if you look in one of those album folders, you will find the songs that are in each of those albums.
But your group folders MUST be in the root directory. Don't have a stick or a card that has a single folder called music or whatever, and then have all your music in that folder. The Boom Box won't find it if you do it that way.
iTunes isn't the greatest software in many ways, but it does a heck of a job of organizing and doing things automatically for you. It would really pay for you to find some tutorials on how to use it or whichever software you decide to use. Look on the apple site and on youtube for videos on how to.
Also, realize that you are not limited to using a USB stick for your CVO. You can use an SD card with a USB adapter for it. The adapters can be found at walmart for less than 10 bucks. I use a 64gb SD card with an adapter myself, and it works just fine.
Also learn about what the speed markings on SD cards or USB sticks are all about. There is a read speed, and then there's a write speed associated with every stick or card. The write speed only applies when you put your music onto the card or stick. But it's the read speed that's important for you on your CVO.
I can't remember if the USB port on the bike is 2.0 or 3.0 technology, but assuming it's 2.0, then it's slower than 3.0 by a lot, and here's what that means:
USB 2.0 read speeds are about 25 megabits per second. What that means to you is that you need a stick or card that is at least that fast, and they'll tell you on the packaging or the device itself how fast its read speed is.
The faster your card or stick is at read speed, the more expensive it will be. Therefore, don't go out and buy the fastest card you can find (say, a 90mbps read speed card), as you Boom Box won't be able to make use of that extra speed, and you'll be spending more money needlessly on the faster card.
But, do by a card that is at least 30-40 mpbs read speed (and no less), as that will be money well spent. This is important if you have a lot of music files on your stick, as you'll want your Boom Box to read them all quickly and then show them to you quickly. Nobody likes to wait a minute each time you start the bike, waiting on your music files to be read by the BoomBox.
Lastly, if you are "ripping" musing from CD's to iTunes or some other music app, rip them at a higher bit rate. Don't opt for 128 mpbs bit rates, as the sound isn't that great. People say it won't matter if you're on a bike, but I can tell the difference between a song ripped at 128mbps versus 320mbps. 320mbps is the highest rate you can rip at and mimics CD quality sound, but you pay the price by needing a lot more storage space on your stick for music recorded at that level. The higher the rip quality, the better the sound, and the more memory the song will take up on your computer or your memory sticks. I rip all my CD's to 256mbps. Again, do the research on line for info on this subject.
Hope this helps.