[LancerX]

I recently purchased a Sansa Clip Zip, and I am looking for a good solution to sync my iTunes library onto it.  Any suggestions?
 
I am aware that one can simply drag and drop music folders onto a MP3 player as if it were a thumb drive.  In this case, I am looking for something more incremental - a program that would only move any songs newly added to my iTunes library since the last sync, etc.  
 
My library is rather large (over 30 Gb), so copying the whole library every time I want to sync isn't practical.
 
PS - Acknowledged that iTunes isn't great and there is better media management software out there.  However, I subscribed to iTunes Match this year to upgrade the bitrate of my old music, so for now I'm stuck with iTunes.

 

[suba3333]

I am not up to date with the latest development but when I got my Sansa Clip Plus about 2 years ago I was also looking into this but could not find anything useful.  For sheer convenience nothing beats the iPod - iTunes combo (automatic syncing of smart playlists and updates of free podcasts).  I still often use my ancient iPod Nano 2Gen because of that even though the sound is much worse than the clip.
 
Your library is still within the storage possibilities of a 32GB Micro SD Card if you want to carry your whole library.
 
I have a 60GB library and a 8GB clip so I have mostly favourites on it.  New additions to my library I often add manually to a dedicated folder on the clip for easy management (either move to permanent place on the clip or remove at a later date).  I use the files structure of the clip (MUSIC>FOLDERS) to manage content on the clip.  So often I have some playlist in iTunes which I copy/paste manually to a folder on the clip.  It's not a big deal but obviously not as convenient as the automatic syncing of an iPod.
 
Hope this helps.
 

 

[Retrias]

Media Monkey is  the software you are looking for, it can autoconvert, then sync WITH itunes, then you can use media monkey to sync with your sansa clip