So this isn't really a Mac issue, more if an iLife or a general Apple ecosystem issue, but not sure where this should go. So if it's the wrong area, I apologize. My new Mac Mini is arriving next week to replace my mid-2007 iMac as my main. I want to get my stuff in order because I'm sick of having duplicate files and a general feeling that my hard drives are a mess. So we will have an iMac, Mini, 2 iPads, and 2 iPhones (and a Kindle ) in the family. I use iTunes to manage my stuff and I let it handle the filesystem stuff on import. Music and Movies(Cinematic Films), and TV Shows, I have no problem dealing with. They are easy to define/manage... I let iTunes do it and can sync what I want/stream to the Apple TVs. Here's my 'problem'... Photos: We have approximately 40,000 photos. About 1/4 are in iPhoto(The ones I've taken), and the rest are on the filesystem. My wife doesn't like trusting iPhoto(neither do i really, but I've given in over the years). So she manages them in Picasa, but ends up having to create 'XXX_iPhone' and XXX_iPad' folders for all the stuff she actually wants to sync to her devices. You can imagine the nightmare this has created, for me anyway. Videos: We have a couple thousand short videos (from iPhones and P&S Cameras), as well as many MiniDV tapes that I'm going to transfer over. These things are really giving me a major headache. We have these all over the place. Some are in iPhoto, some are in my wife's folders from her iPhone. We use the iPhones a LOT for video. Some are imported directly to iTunes as 'Home Movies'. What really gets under my skin is when these things are 'copied' into iMovie. We copy them because we have the files in our respective messy folders already. So we end up with iMovie events that are humongous and iMovie projects that are eating up space. Then we have iDVD projects(yes we still use that) that are eating up gobs of space. All these app created directories seem like such a stinking waste to me. So photos and videos are really the main issue. I really don't want a gigantic iphoto library with 40,000 photos/videos, but if I want to use these on the iPad/iLife I need to. Can't have multiple libraries cuz iTunes no likey. iMovie doesn't allow you to sync videos unles you create a project, so it's not like I can use iMovie to manage all the short clips and sync them with the iDevices as well. Ok. I know this is probably way too much info to deal with here... but... I needed to get some work on my BT Keyboard on my iPad So help me out here... I just feel like this should be easier using the Apple way. But it seems like the Apple way is more difficult. I want to be able to manage these digital assets smartly, while being able to sync the individual assets as well as any projects created with them with the iDevices. Maybe I'm just stupid. Thanks for reading.