technically a ZIF drive is recognized as any other IDE/PATA drive by the system
a ZIF to USB Adapter could help here if you a using rockbox for easy drag an drop of your media files but I am almost sure this will never work with iTunes since it wont recognize the connected external drive as an iPod but just as a regular drive
I have a suspicion this will not work with a 5.5 gen.
There are three problems here:
Firstly if using iTunes and the OF for playback, it won't work for the reasons cis gives, due to the way iTunes behaves (but there might be some way round it).
Secondly, even if _not_ using the OF for playback and iTunes to sync, I think it won't work because the 5.5 gen and later use a non-standard kind of disk formatting that isn't recognised outside of the ipod. It _will_ work for a 5th gen, won't work for a 6th gen or later, and I don't
think it will work for 5.5gen but am not sure about that case.
Finally, as you are using a multi-card adaptor, you can't just do it by putting the card itself in a card reader. With the single-card adaptor or the ssd adaptor, plus a 5th gen, you could actually sync that way (I did so at one time). But with the mutli card adaptor you would have to put the entire adaptor in some suitable enclosure/reader, not just individual cards. Not sure what reader that would be, and it would have to be one that didn't itself have a 128gb limit.
Mainly I think you just have to attach the modded ipod, start syncing, and go away for a weekend! It's only a problem on the first full sync.
Don't forget to tell windows not to go to sleep (I bloody _hate_ how windows 'sleep mode' thinks the PC is idle when there's no mouse/kb input, even when it's actually busy running a back-up or sync or some other important job - computers I used to work on decades ago could figure out when they were genuinely idle or not, why does Windows have such trouble with the concept?)