Can't sync music to iphone 3GS from new computer

I have always synced my iphone to my husband's PC since that has always been our music storage machine, but would like to sync to my macbook.

I've set up itunes Match on both machines and downloaded our music to my mac - mostly itunes purchased or uploaded from CD. I hit sync and agreed to have it wipe the contents from the other computer and sync with my mac. When I do, it only copies about 100 of 1000 songs, saying it couldn't copy the others. It referred me back to itunes to find out the issue, but I couldn't find any explanation in my itunes for the problem. (The missing songs show up greyed out in the playlists on my phone)

I'm sick of fighting for computer time when I'm trying to set up playlists for the fitness classes I teach so I'd love to use my machine.

Please help!

Thanks.