My only experience with such programs is Emplode and Rio Music Manager -- both of which are vastly superior for my usages.

To add music to my player with Emplode or RMM, I find the files, drag them to my player, click on "Synch".

To add music to my player with iTunes, I find the files, tell iTunes to add them to the iTunes library. Once that is done, I delete the files from the iTunes library that I no longer want in the player, then copy the files in the iTunes library into the Playlist library. Next, organize the Playlist library so the tracks (audiobooks, in this case) are in the proper sequence so that chapter four comes after chapter three. Check the settings to make sure that the "Random" box is unchecked, then click on Sync, in the full knowledge that my placemark in the file I was last listening to will certainly be lost so that I have to search through the book to find where I left off.

[RANT]I know that some of this is "It's different from what I'm used to so it can't be any good" attitude, but every time I use Apple software (particularly on SWMBO's Macintosh) it is an excercise in absolute frustration that makes me want to throw things. There seems to be no middle ground with Apple: Either you operate at the absolute dummy level and let the OS take care of everything, or you become an absolute Macintosh expert in order to find out simple, obvious things like just where in hell a file you downloaded is actually located on the hard drive. SWMBO downloads pictures from her camera, the Macintosh sucks them up and stores them someplace and she can view them anytime she wants with some sort of Macintosh picture viewing software, but God help her if she wants to attach one of them to an email. Apple's policy of hiding all the ugly nuts and bolts of system level operations from the user makes me crazy. [/RANT]

There, I feel much better now.

tanstaafl.