iPod 5th gen + RB/OF + iTunes + iFlash Quad

[anchanjerica]

Okay, I'm wondering how well this will work for me.

I'm getting an iPod 5th gen, getting the iFlash Quad, and have four SanDisk Ultra 32 GB Micro SDHC cards. I'm going to use iTunes to sync music to it since, well, I actually like the management in iTunes from a computer side. What I don't like is how restrictive the OF feels.

What I want to know is, using iTunes and OF for syncing, will Rockbox have a fit with the tracks on its side? All my tracks are either mp3 or AAC files, a number purchased (DRM free) iTunes tracks and almost all not from iTunes ripped from my own sources to high quality AAC. I don't care for lossless, I just care for having a bit more flexibility in controlling my sound tuning and user experience.

[Frankenpod]

If you sync with iTunes the tracks will use the weird obfuscated naming system that iTunes uses (presumably that was some early primitive and pointless effort at a kind of DRM?).  But Rockbox will still be able to see them and you could still use Rockbox if you build rockbox's database and all your tracks have the tags correctly filled in.  If the tags are incomplete or not correct it won't work very well.  The file-browser will be useless with apple's messed-up directory structure so you have to ensure the database can build properly.

Edit - doing it that way will also make it tricky to use any playlists you made on the computer.