I would say turn on the RRMedia debug options. With RR running, right click the RRmedia icon in the system tray and Open storepath locaton, then open up the RRMediadb.ini file.
Set both of the debug options to true under the [General] section, save, close. Then close and restart RR.
Go thru same process as you posted above then Attach a zip of all the xx_debug.txt files found also in the same folder that the ini file was.