In MC you can create any number of virtual "HandHelds" and sync them.
For example, you can configure a virtual HandHeld to automatically sync a smartlist that includes only the five star rated files. It will then copy the files to the defined location and folder structure and also automatically convert any unsupported formats (if set to do so).
I attached a screenshot of my current virtual handheld settings. The root location is F:\HH\, the name of the virtual device is "F HH", and the audio folder path is defined by the "if(isequal([Media Sub Type],Podcast,1),Podcast\[Album],Audio\[Album Artist (auto)]\[Album])\" rule (i.e. since I mostly sync complete albums I prefer that the standard audio files go to the "Album Artist (auto)\Album" folder structure, but if the file is a podcast episode it goes to a different location. Normally I use only "drag and drop" syncing, but I could also sync any predefined static or smart playlists.
Here is another screenshot of my settings (and a related discussion) from last summer:
http://yabb.jriver.com/interact/index.php?topic=64858.msg434701#msg434701Log in to the forum if you can't see the attachment.