Oh yes the Connect software sucks alright. I don't understand how hardware manufacturers can keep doing this. They need to start hiring professionals to write thier software instead of getting thier kids to do it /rant.
I managed to get Connect software to upload a few songs.
I also made the mistake of getting it to catalogue my (35gig) MP3 library by itself. Since then it takes about 10 minutes just to start, and won't upload songs to my player.
Also you can't use it for organising MP3s cos it takes about a minute to write out a single tag (I have a top end PC, AMD64 3800, Dual 7200rpm SATA in striped RAID config etc).
I use SonicStage now instead, which is 10 times better, but I could still write something better in my lunch hour.
What Sony need to do is release the API for interfacing with thier hardware and let real programmers write the software using GPL licensing.