Moved your post over here where you can more help from the helpful Captivate gang. Offhand, I can offer that lots of people seem to like Doubletwist for that sort of thing.
I just use drag and drop via USB myself, as opposed to syncing.
Google 'Double Twist' for either your PC or MAC. It will put your itunes music onto your android phone so long as the music is DRM free. Some of your music you have downloaded in the past may not be DRM free but Apple will let you upgrade some of your songs to DRM free files at a cost.
I did this with my library as its as old as 2003. Some of my Songs had to be upgraded to DRM free. However there are some songs that iTunes does not have in their library anymore or do not a DRM free copy. As such I was able to put most of my songs on my android but not all. However I believe MOST or everything now on iTunes is DRM free. So you shouldn't worry about downloading any new music.
The other option is to use RDIO, which scans all of your music in itunes and lets you play your files over the air, aka streaming. However this service is about $9.99 per month and in some regions doesn't let you stream all of your files. I'm in Canada and only half of my songs were allowed to be streamed to my android phone. It also lets you have offline files on your phone if you don't want to stream the music. The cool thing is you can download and listen to as much music as you want for $9.99 a month.
I've had a lot of luck with TuneSync. It lets you wirelessly sync iTunes playlists of your choice. There is a small server you install on the machine with your iTunes but once that is done you can manage everything from your phone.
Last I checked AirSync for DoubleTwist which let you do wireless synching did not work right with the Captivate's SD card configuration (if you want to put your music on an external card)
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