Its hard for me to help, because i have never had any problems. Are you on Vodaphone BTW? They have some wierd restrictions on files and sizes for some reason.
All i have ever done with mine is rip a load of MP3's, put each albums MP3's in a folder of thier own, then dragging the whole lot of folders and file over to the phones MP3 folder (somethimes over 200Mbs of music, with files averaging at 4Mb each) in My Computer. Then i disconnect the phone, go into the media player, created a new playlist and select a whole folder. And this is with the bug-tastic orginal firmware.
You might have more luck searching on the www.howardforums.com
