I tried a few free tools such as Winamp, EasySync etc. With Winamp, the sync was never perfect. There would always be some files that needed to be copied over to the device even though they were changed. Also there would be files on the device that had somehow become ‘new’ and had to be pushed back to the library on the computer. After trying out a few more, I decided to do it my way
First off, download Microsoft’s Richcopy tool. This is free. What it does is to copy (or move) files that have changed only; it compares the file attributes to those in the target directory and does its job. The first copy is longer if the number of files is large. The good thing about using Richcopy is it maintains the folder structure of your library. I like to keep the music organized by album much like a CD has an album. Some of the syncing tools copy the tracks into the artists folder first or a track number – didn’t like that.
Second step is to use Winamp to import the iTunes playlists into Winamp. Then you can save the playlists as m3u files. Copy these m3u (playlists) file over to your device to the same location as within the library and you are all set.
Whenever I add a new file to the library or change the tags, then all I need to do is repeat the two steps above and it is way much shorter. Now I have more control of the synching process myself.