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Use the program called Windows Media Player to transfer songs to the GoGear. A full version of the user's manual is available at www.usasupport.philips.com
The sync error could be deeper - you are going to laugh, but many of the "Rhapsody" enabled Philips GoGear's are incapable of playing most Rhapsody songs. You may be getting the error message because your music service is giving you songs in DRM-encrypted WMA format, and the Philips is incapable of reading that format. Ironically, the older Philips can read that format - most of the newer ones can't.
The songs are in the wrong format - they are probably DRM-encrypted WMA files that you are trying to transfer, and the license on those files are wrong; they are either "fixed-term" or lack "transfer rights"
To resolve, either upgrade your music svc subscription, or convert the songs to Mps format
Sometimes you may have a bad sector in your hard drive, you may want to remove that song from iTunes, sync (which will take it off your iPod) then add it back into iTunes and sync again (to add it back on, likely in a different spot on the hard drive). If this does not work, you may want to try and convert that song to another format and then convert it back to MP3.
A fix for now is to right click and get info on the song and go to the options tab and tell it to start 1 second into the song.
I had this problem also and I think I figured it out because now my music will play. I took the songs I had from limewire, highlighted them all and clicked "save as", opened it with windows media player and on wmp I took my playlist and named it on there....first I synched the songs under "sync" and they would upload on my player but they would NOT play. I got the same stupid error message. So after they were uploaded onto my mp3 player, i dragged all of the songs onto the right side to make a sync list AGAIN and clicked start sync, all of the files said "already on device" so I kind of got mad thinking it still didn't work...when I unplugged it and tried to play the song, they ACTUALLY PLAYED. I fought with this for so long and contemplated about throwing the stupid thing down the toilet but for whatever reason, synching it in two different ways in that order, it worked and it stopped saying "error:can't open this file"...hope this works for you and anyone else having this problem because I know how frustrating this got for me. hope this helps. Good luck!!!