It's my understanding that as long as AMDS is properly installed and running, third party software should be able to talk to an iPod Touch and iPhone to load both content and playlists.
AMDS=Apple Mobile Device Service, which is (more or less) the Apple-specific USB device drivers for windows.
The iPod Touch and the Iphone 4 require the most recent available version of AMDS (v17.58.0.something seems to be the latest). The installer .msi can be extracted from the iTunes download with something like 7Zip or WinRAR.
Does Apple have an available SDK/API that talks to AMDS?
Or perhaps the 'correct' way to sync a Touch/iPhone with MC is via an applet? Instead of pushing the content in via the PC side, have an iPhone applet that **pulls** content made available to it. Assuming that the Church of Jobs and Dear Leader would approve of such a thing.
An applet that is pull-oriented might be the way to go with Android devices as well. Put some of the onus for sync on the device itself. These are, after all, supposed to be smart devices with gobs of ram and gigaherz processors. And a set of app stores. Might as well take advantage of them. Posting applets in the Android and iPhone app stores might be a sneaky way to get publicity for MC as well.