Sounds like similar symptoms! I had a small USB Flash Drive attached and used a thin strip of Guerilla Tape to "secure" the drive to the socket. Also then Guerilla Taped the assembly to the roof (top) of the saddlebag so avoid "swinging" (movement) and such to avoid stressing the connection. So, weird indeed that it started up for no apparent reason with the stop/start/restart thing. Anyway, the new Flash Drive is just a cheap one (trade show bling) and with the FAT32 formatting (not Quick Format), it seems to be working fine -- taped-up as before. Time will tell!
I used velcro to attach it to the inside top of the saddlebag.
Only issue when using Pandora on bluetooth, if my phone rings, music stops and a voice in Chinese voice announces caller. I simply wait to go to voicemail and music starts up again.