I re-read my post, and realized I should have been clearer. I took delivery of a standard range Model Y in March 2021. It has one USB-C, and one USB-A port in the center console (underneath/behind the wireless charger). I've also got a USB-A port in the glove compartment.
For years, I used the USB-A in the glove compartment for dashcam/sentry, and the USB-A in the center console for music. A few months ago, and after a software update, the USB-A in the center console stopped detecting the USB flash drive that contained my music. The flash drive is opaque, and I could see a red light go on, indicating it was receiving power. I tried different flash drives, including the one that originally came with my Tesla, but none of those worked in the USB-A port in my center console. I reset the car, yet nothing would get the center console USB-A port to read my USB flash drive.
A week or so ago, I finally tried using an Anker USB hub with the USB-A port in my glove compartment. For me, this has fixed the issue, as the vehicle immediately recognized the flash drive w/ my music. Since then, I have not lost access to that flash drive, even after the car goes into a deep sleep state.