Why does it need to be 30 pin line out?   If you really just want 30 pin line out you are limited to the older ipods.   There are many different options out there for just standard 3.5mm line out, check out the Fiio line up for example.

Try using a tool like MP3Tag, you can use it to re-name your files using tag data, so I have mine set to pull the tag info and rename it as   %disc number%-%Track number% %Title%,   you can also use it to set your folder structure, so   /%Artist%/%Album%/%disc number%-%Track number%...