That's why I keep Sirius active. Someone else being the DJ is nice. A little talk between the tracks is nice, sans ads of course. Streaming services work too but seem to be a bit more repetitive sometimes. Not that (any) radio is free of repetition, of course. But if/when that happens it's an immediate change to a different sat channel. Switching streaming 'stations' is more tedious (as in, dangerous while at the wheel) and takes waaaaaay too long to re-buffer.

There's a PC program from J.River, Media Center, that's very handy for wrangling media tracks for copying to devices. Be warned, it's like a foot-wide swiss army knife... it has features for EVERYTHING. Not always the easiest to use though. But it's got a really powerful copying tool that can take tracks from your computer and put them into completely differently named folders and files. Which can make it easier to browse through them on user-interface-impaired devices like car radios. So while you might use one artist\album\really long track name.mp3 format on your computer, you could copy them as music\a-g\artist\album\track#-trackname.mp3.

 

I RIP my CD's directly to the thumb drive (then copy the rips to my computer based music files) using "FreeRIP" - which is a Windows program, quite capable and FREE (although I did donate some $$ toward it since I use it so much.)

In FreeRip - I've setup a configuration on it that saves the music as:

ALBUM - AUTHOR/PERFORMER
-- Track blahalabla
-- Track blahahaha
etc..

Basically a directory (folder) named after the Album Name, then with the Performer/Composer info. In that directory - all the tracks from that CD.

FreeRIP "rips" the average CD in about 45 seconds, so it's not like you have long conversion times. That made it practical to convert all my CD's to MP4 format. You have a choice of formats including the Apple Lossless one in case you want that.

If you go with FreeRip - let me know - and I'll post the "mask" I use for creating that structure.