Since you are Apple-less, I'm not aware of any good automated solutions that will help deal with MS' present challenges. From months of experimentation, IMHO it comes down to your priorities working within the limitations and quirks of Media Player.
I've now gone through 3 different major organizational schemes... The last one as you found in another thread is an "Apple-only" solution using TeslaTunes (which modifies tagging of tracks onto the USB sticks to workaround MEdia Player quirks) that I'm about as happy with as I'll be until Tesla revamps Media Player -- but the first two things I tried may be something you can consider... Each has benefits and different drawbacks. Rather than retype it all here, if you are interested in a description of each, go to my personal website here:
Tesla Model S: Listening to Your Own Music Library • Bert's Place Click the large "+ USB" slider, and keep scrolling down to a section called "No Playlist (M3U) Support". My first two attempts are outlined there, including the reasons I abandoned each one for the next -- but both should work fine copying tracks in a Windows environment and make things a little better than just dumping large numbers of tracks onto a USB stick and praying for a good result. You'll just have to decide if the trade-offs of one or the other is better for you than what you're already doing. Good luck.