I started ripping CDs years ago, not for the truck but for other systems. There's hardly room in my cab for a cup of coffee and a jacket so I am glad I have the digital option. Glad I don't have to manage CDs. But I live in greater Los Angeles and I get good reception with lots of station choices, so I listen to FM Rock and Country mostly. And I will admit to listening to my CB a lot too.
Anyhow, I'd start ripping the CDs to mp3.
Here's what I do. I use the directory structure for Rock, Country, Christmas. as root directories. Then I have a sub directories with all Led Zeppelin and subs for each of their albums same with Beatles. each band or artist has it's own directory structure under the genre root.
When you flip through the directories the display will show where you're at. If you choose random at the root. then you get random tunes from the structure below.
Or you can just listen to an album in it's directory. It is pretty clean and easy once you're set up.
j