I'm not dealing with FLAC nor anything already on the device. Although I do have a few M4A tracks. I do have some video files and I don't think they're being transcoded.... I'll have to check.
Meanwhile I've just set up a device from a drive letter pointing to a network share. I then sync to that and manually drag the files over to the portable player.
The problem is the sync program is being too smart for it's own good. On one hand it understands the tracks would require more room that fits. But on the other hand it's ignoring that format conversion has been selected; which will result in smaller (as yet to be computed) sizes.
I'd like there to be a per-device option to ignore the size of the device. I could see where this could present a problem in that the sync handler would have to be able to (gracefully) deal with running out of space. Thus a checkbox that let's me make that call would be nice.
As for on-device media and its impact, that might be good to bring up in a separate thread.
I sort of ran into that and kind of asked about it, from a different angle. Here:
http://yabb.jriver.com/interact/index.php?topic=93196.msg642498#msg642498I asked about rebuilding a playlist from media that's already on a device, but using tracks from the database (not the on-device ones).