If I am listening to USB and on Shuffle mode, restart the jeep and usb back to orginal 1st song and no shuffle mode. I get lucky sometimes and it stays on the last song.
I never tried a USB stick, I use Android Auto with spotify to listen to anything I want seamlessly from home to car to gym etc...
If I did not have a streaming service, I would load a ton of music to my phone and use a media player app on my phone to manage and play music how I want. Gives more flexibility than a USB stick.