I think apostrophes are a complete no-no for Sooloos in the filename. If you look at the original files in Finder, check there definitely aren't any non letter characters. I would be tempted to just rename them to something very similar but with only letters.

On the Mac, try downloading a tag editor and have a look at the meta data on the FLAC files. Just check there isn't something odd looking. I have had Control:Mac throw some very strange errors if there is odd meta data, even though it is then going out and getting its own meta data. One set didnt have the number of tracks set correctly and that screwed it as well.

I have had some very odd errors in the past, but have normally got around them eventually, but its trial and error, unfortunately.

Cheers
Greg

M owner since '97