Don't know if this is helpful, or just the solution to an asked question...
Got a shiny shuffle for crimbo and love it
The downer was using iTunes to synch the music - boy does that program suck; slow buggy and the final straw was when I loaded up iTunes with out my (external) media drive connected and as the prog couldn't find the files it deleted them off my iPod 
Fired up MediaMonkey and everything was great until I realiesed that music copied across played in its own order - sort of a one time shuffle. I am not so keen on the shuffling concept - well not being forced into it anyways, so if anyone else is suffering from the same problem do the following:
In iTunes, set the Shuffle to be useable for files.
Make sure you are using the latest version of MM - I was using 2.4.x and things got better after upgrading. Watch out though, the file links on the download page are broken today. Steegy helpfully posted a link to a beta (installed + seems stable) at http://www.mediamonkey.com/beta/MediaMo ... .5.989.exe
Go to http://www.mediamonkey.com/beta/d_iPod.dll (thanks skst) and download the beta version of the iPod dll. Once downloaded, go to the plugins driectory in MM, remove the old version (or copy it else where if you want to be safe - DO NOT rename it ...bak or something - I thought I had broken MM badly for a while thanks to that mistake...), then copy the new version of the dll into that folder.
Make sure that you have right clicked on the shuffle in MM, slected properties and then ticked Force iTunes style folders.
Fire off an irate e-mail to Apple suggesting that they either learn from the MM dudes or just give in and ship MM on the player to give users a choice! It's not like they bother to put anything vaguely useful like the manual or iTunes onto that 1GB of pristine flash memory. I mean, honestly - then they take the support files off line on Christams day... growl...
Anyways, hope this helps someone...
Dave
