Just as I was starting to wonder how long it had been since I had this issue (maybe fixed!), this weekend it failed miserably.
It took 15 minutes of multiple reboots and multiple plug / unplugs to get it back. My stick has USB A on one end, and USB C on the other, so I was able to try both the glovebox and center console ports. I had better luck with the center console ports, but it was still hit and miss. I put in a service ticket this time around, expecting it to be cancelled but hoping it will be another data point for the company.
Incidentally, I use a USB to Micro SD adapter, with a high endurance SD card designed for dashcams:
There are 2 things unique about this setup that I suppose could be causing the issue:
1. There are 2 ports on the stick, one SD and one micro SD. I used to have persistent USB not formatted errors (but dashcam/sentry still worked fine) that turned out to be due to the second slot being left empty. I plugged in an old SD with a bunch of music on it and that error disappeared (and the music works too).
2. My MicroSD is 256GB, which the car couldn't format itself. I had to format it using the computer, and again it worked fine.
I don't know if my "non-standard" setup is causing it to still have issues or not. Maybe I'll try a stint using the default Tesla stick and see if it comes back...