Since the program is not intuitive (like your photo app) have a 'Wizard' option, which asks 'what do you want to do?' then goes through the stages, eg do you want to add a the contents of a folder, to your iPod Browse for folder, and the program would automatically do that. The 'Do you want to add this folder to a playlist?' Choose from list plus new/create. Then do you want to save this to your iPod? Program would do it automatically...

The best way to do this is to watch someone trying to use your program, without helping them at all. Look and see where the sticking points are - it does not matter if they are obvious to you .. are they obvious to the user? ' I.E. apply the 'Granny test'. I realise this one is more awkward than the photos because you have to fit in with the relics of iTunes on the iPod, but I still think you could make it a lot easier?

I am not being rude to grannies . I am an ancient one myself, and I started to write my own programs and web-sites back in 1993, but I still think the best programs should pass the 'Granny test'!