I wanted to find out what strategies some of you have found helpful to streamline and simplify the process of organizing and syncing your iTunes media to your iPhone (or iPod Touch/Video iPod, as well as to your Apple TV if you have one). I figured I would start this thread by posting what I've found to be one of the most useful tips for streamlining said process, and then perhaps anyone who has any good tips to share might reply and spread the wealth of their knowledge... -------------- My organizational dilemmas with iTunes seem revolve around syncing/organizing my videos...I often have two copies of a particular movie/TV show (one that's optimized for the iPhone, and one that's optimized for the ATV). I also use iTunes to store and view movies I've downloaded off the internet (from YouTube, etc...), and these video files don't really look too hot when viewed on my 50" Plasma, so I prefer not to have these synced to the ATV (I'd rather use the ATV's built-in YouTube Browser as needed). All this leads to a massive collection of videos with little to no organization, which makes syncing, organizing, and even just finding a particular video a real pain in the butt... HERE IS ONE OF THE BEST TIPS FOUND that changed the way I organize and sync to my iPhone and/or my ATV: I'd previously kept all of my iTunes videos (that weren't purchased through the iTunes Store, obviously) clumped together in one huge list that was accessible from the 'Movies' section of iTunes (which is the default section of the iTunes library that newly added videos are added). This quickly became a major pain - having to scroll through hundreds and hundreds of movies, web-video clips, untagged TV shows, etc...to find what I wanted to watch, or to check files that I wanted synced to one device or another... One of the less hyped features of iTunes 8 is the ability to change the "Media Kind" of a particular video file, and the tip that has changed absolutely everything for me is as follows: Select all of your YouTube videos (for example) from your huge list of video in the 'Movies' section of your iTunes library, then choose the 'File>Get Info' menu item (Cmd+I on Mac; Ctrl+I on Windows)... Click the 'Options' tab of the Info window, and change the "Media Kind" to "TV Shows". Then, using the YouTube video we've just selected as our example here, change over to the 'Video' tab of the Info window and change the 'Show' to something like 'YouTube Videos'. You can then optionally flip over to the "Info" tab of this Info window and drop in an image file into the blank area next to "artwork" And, before you do any of this, if you have the iTunes Preferences settings configured to "Keep iTunes Library Organized", then doing this will also move the actual YouTube Video and place them neatly into their own little Sub-Folder named "YouTube Videos" within you iTunes/Music/TV Shows folder. View the screenshot below to see the results of the aforementioned strategy for organizing videos within iTunes: You will see that I have several regular-old TV shows appearing in the list just as anyone would who purchased some shows from the iTunes Store, but you will also notice shows called "YouTube Clips", "JibJab", "Politics", "Educational", "iPhone Essentials", etc... This is a brilliant way of keeping all of your similar videos files organized into "Virtual Folders", AND PERHAPS MORE IMPORTANTLY, it makes syncing specific groups of videos to your iPhone or Apple TV as simple as can be, because you can simply specify within the iPhone/ATV sync settings which specific TV shows you want to sync, and which ones you don't... In the screenshot below, you will notice a show called "iPhone Essentials"...this is the show name that I've applied to the JibJab, YouTube, Educational, etc. shows that I definitely want to have with me on my iPhone...I have dozens and dozens of web videos within the YouTube Clips 'Show' directory, but not all of them are things I want synced to my iPhone...hence, I created the "iPhone Essentials" show directory which is basically a drop box for any movies I definitely want on my iPhone Anyone care to share any of their Killer Strategies for Organizing iTunes Media for iPhone/Apple TV Syncing?