Q: Is support for the newer (2009 and later) models planned?
A: No, and there will never be. The database format has changed completely between the second and third generation iPod shuffles. Supporting it would amount to an (almost) full rewrite of the program. Even worse, it's not even certain that it would work at all: There's a high probability that the new database format is not manageable with rebuild_db's simple just update one file and be done with it approach.
edit I have programming experience and I know it wouldn't be hard to just generate every song in a random order every time the ipod is plugged into the computer, or turned on to shuffle and then just play through that generated playlist of songs on the device.
Unfortunately gnupod isn't exactly that user-friendly. For one, it isa huge pain to add a list of files. It isn't smart enough to read am3u playlist and just load all the songs in order. Ugh.Fortunately, I've written a handy script that automates all thatnonsense. Download my ipodshufflescript somewhere. At this point you're good to go.
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