Yeah, it actually needs mediamonkey to set the gapless tag information on the ipod DB I believe.
I did test it with my new 80GB ipod. I synched an album I flagged as gapless in itunes - worked. I reset my ipod and resynched that album via Media monkey and it wasn't gapless. I wasn't expecting it to work but tried nevertheless.
I've unfortunately had to revert back to the loathed and still buggy itunes now - gapless is that big of an issue for me. I just keep checking back here in the forlorn hope that MM will update it's ipod dll.
I would be happy to put my programming skills to use to help...
It is great finally having gapless playback at any rate. I can't believe it has taken companies so long to get this rather crucial audio playback issue fixed (after the ill fated rio karma). I'm just really ticked I have to use itunes to get it... I really do hate itunes.