Does anyone have ANY suggestions in a good direction to go on this? I've been meaning to learn Applescript recently, so i'm up for some work if it has a good result. Here's my situation: Originally, I had been ripping my CDs at 192 AAC because I figured that would handle any problematic songs that might not do well at say 128, and it would be acceptable to listen to on my home stereo while not taking up too much space on my iPod (about 5,500 songs on a 30 gb). However, Apple Lossless Encoding and Airport Express have kinda turned my world upside down by making some new things feasible finally. I live in an apt and my 1.25Ghz powerbook is never far away, but I hate plugging an audio cable in to listen to iTunes through my stereo. Airport Express will solve that problem AND finally provide a digital out to iTunes which I have grown to love. The addition of a digital out kinda makes me want to take advantage of it's greater quality output. Since hardrive space is cheap (I have 80 on my powerbook, and another 250 external LaCie firewire 800 drive, and I'm about to get another 250 I think), I'd like to rip all my CDs in ALE and let this be my main music source. I figure at this point I can either buy another 400 disc CD player for another big ass hard drive, which both cost the same (about $300), and the hard drive gives me greater control over playlists and all that. So, what I'd like to do is rip everything using Apple Lossless, but since I don't want to use thse huge files on my iPod, and since I don't need the 192 on my iPod since these songs would no longer be doing double-duty as the source of my home listening material, Does anyone have any suggestions on how to manage 2 copies my music? I'd like to keep my sanity...somewhat, if at all possible. But I'm for a bit of juggling. Essentially, I'd like to keep Apple Lossless songs off my iPod, and make sure that the lossless version is the one that's being used at home. One complication to all this is that I have a bunch of songs that I didn't rip from cds so i don't want to just only listen to ALE files at home, i'd like to somehow be able to switch between the two versions of all the songs that I do have the 2 copies of. I think I can handle that with a simple script and something in a comment field simply indicating that it exists in both formats. I am wondering if there are ANY ways that I could automatically keep both copies of these songs in playlists that I create? Are there any applescripts that already exist to help with any of this? Anyway, thanks guys, this place is awesome!