I found this thread after searching the forum for a solution to similar issues. I would like to transition to MediaCenter for syncing my devices and replace my current solution. I think its worth resurrecting and I think some feature development would be helpful to more people.
Matt,
I have found (in general) that most car stereos (especially factory units, but a fair amount of aftermarket head units as well) do not support playlists (at all). In addition, I have found that the head units' ability to handle/play/manage audio stored on removable media (USB, microSD etc) to be very limiting. In general, the implementations seem to not want to deal with the file/folder and absolute/relative paths of playlists and audio organization. As an example, some units will only let you 'randomize' across a single folder on a USB stick. If you have the standard \album\artist\track system than this means you can only randomize across an album. Other head units have very very poor randomization or none at all. My wife's car resets its randomization to the same spot each time you start the car (seed = 0). So the 'random' list is actually a deterministic list that repeats itself.
The only real way to work around these issues is with a playlist based folder system. So if I have three playlists (playlista, playlistb, playlistc), the folder scheme on the usb storage is:
\basedir\playlista\(track1..n).mp3
\basedir\playlistb\(track1..n).mp3
etc...
I am currently solving this problem with a very long and complicated perl script that performs device syncing for me. (And the script is currently tied to iTunes using its COM interface, since there are some iPods in the household.) And for each device, I can specify whether to sync by standard \album\artist\track or by \playlist\track. I then create a master playlist with all tracks on it (and now I can simulate random playback across all files), and separate playlists for any other mixes. This will mean that multiple copies of the same song are present on the usb, reducing space, but it gets around the major deficiencies of the various head units and devices.
As maintenance and management of the script has gotten to be unruly, I'd really like to transition to MediaCenter for device management. I was happy to see that many of the features I have in my script are already in MediaCenter (like selecting which audio formats the device can support, and automatically transcoding if needed).
Being able to sync the device by playlist folder is the one major missing piece. Having a database term like [Playlist] or [SmartList] would allow setting up the audio folder paths on the usb device to match.
Maybe this is something to consider for MC19
?