I'm not sure how the play list is remembered between restarts, so that the songs start where they left off.
In your case this isn't working, why?
Does the car have to store something on the USB stick or something in the player to remember last played position?
If it's on the stick, and can't write to it, is it a permission problem?
I wonder if I can find something on my USB stick, or I could just ask google.
Back later.
Found this on a Honda site.
"Welcome to Honda's categorically inferior infotainment system. It works that way in all their cars and has for at least three years. This is what works in our 2016 Pilot....just before shutting the car off, change the input source to something other than the USB stick. Then, next time you start the car, switch back to the USB stick. It should pick up where it left off and not go back to track 1. Big PITA."
May be worth a try, but as some of us don't have the problem, don't hold your breath.
Some one else mentioned it will only work if the USB stick is formatted in FAT32, if you have a stick bigger than 32GB that may be difficult, it will want to format in EXFAT, but it can be done.
Good luck!