Hi Kai,
Not sure why the web UI upload is not working except perhaps the WiFi signal at the BB1 isn't good enough. You can check this by using the top control to go to Main menu >> Settings & Tools >> Maintenance >> Advanced > WiFi Strength. Ideally this should be around -50dBm (where -40dBm is a stronger signal and -60dBm a weaker one) for a reliable connection.
For the USB transfer, make sure the music is arranged as follows -
music - a folder - must only contain Artist folders
Artist #1 - a folder - must only contain Album folders - no Tracks or other files
Album #1 - a folder - containing Tracks and album artworks (.jpg)
Track #1 - e.g. Here comes the Sun.mp3
Track #2
etc
Album #2
etc
Artist #2
etc
music is not required but does group all of the Artist folders if transferring multiple Albums.
Paul
Brennan Support.