I don't know what most other people do with iTunes, but I keep two libraries which are duplicate of each other. One is stored in Apple Lossless and it's a combination restorable backup of my real 375+ CD library and the highest sound quality I can get from them to use in my whole house audio system. It takes up over 120GB of space (I use two 500GB hard drives; one as a backup mirror). The other library is a 256kbit conversion of the main library and I made and use this so I could fit more songs on my iPod Touch (which can only hold 16 GB before formatting, etc.). So the 256kbit version of my library lets me squeeze more songs onto my iPod, but it's also a bit of a pain to use. Not only did I have to convert the entire library (which took some time with that much data), but even once it's done, it's then a pain to add NEW music because I have to add them to both libraries! So it's either insert CD and import twice (having to switch both libraries and the directories where the files are put first; I have to use a 'buffer' in-between change empty library there as well before changing the directory or iTunes starts screwing things up) OR I have to import once and then do a copy/convert. Both are a pain in the butt to maintain. Now when I want to use my iPod, I have to remember to swap libraries again (quit and restart iTunes holding down the ALT key) or otherwise the device not only gets confused (since it was synced with a different library) but I'd be staring at lossless files anyway. Of course, once you have your music on it and just want to update apps, that can still create problems if you forget because iTunes can still get confused since it was synced with a different library). Now it seems to me, ALL this extra bother and frustration could have been avoided IF Apple simply had an option to convert songs being transferred to an external limited device like an iPod to your favorite compressed setting on the fly. "Sync to 256kbit" for example would be a nice option. Then I could use ONE Lossless library and still have compressed music on my iPod. This might take a bit of extra time to sync, but given how SLOW iPod Touch syncs are already, I'm guessing it wouldn't add that much at all (but would drain CPU cycles during the sync). OR Apple could provide easier dual library functions. For example, it could offer to automatically create and keep a 2nd compressed 'portables' library and automatically convert new songs added to that library at the same time or shortly after creating the primary (lossless) library. It would then be set to sync from the portables library so-to-speak not the main one. Now even IF Apple couldn't be bothered to add THAT kind of support, they could STILL have better support for existing libraries. In other words, I don't add new music THAT often. I already have both libraries set up so it'd be nice if I could at least access that 'portables' library I made without having to 'switch' libraries. If they'd simply offer a secondary library in the panel like they do 'shared libraries' and let me make playlists from that to then sync to my iPod, I'd be all set. I'd never have to screw around with changing libraries and settings just to sync my iPod. Really, most of this seems like a no-brainer to me given Apple knows iPods cannot hold many people's large lossless libraries. True, not everyone uses lossless libraries and I'm sure Apple would prefer you buy AAC files instead of CDs to make lossless libraries, but they DO have lossless support and that does create the above problem and they COULD easily solve most of the 'pain in the butt' issues in an update.