More Efficient Way to Organize New Music/iTunes/External HD?

Let me disagree with the posters above. Yes, Apple's software (iPhoto, iMovie, iTunes) is there to add a layer of abstraction between you and your actual files. And for some, perhaps it's enough to be able to go to iTunes and do "Show in Finder/Windows Explorer". However, I like to have my data logically organized irrespective of any application I choose to have access that data, and not give up all control TO that application. (And I'm almost exclusively a Mac user...so I'm rare). So do not listen to the people above and check that "keep my music organized please, Mr. iTunes" box. It has even been rumored to delete some songs if you do... http://forums.macrumors.com/showthread.php?t=394843, http://ask.metafilter.com/79424/Is-Itunes-deleting-my-music-And-why-wont-it-load,http://ask.metafilter.com/123223/iTunes-is-randomly-deleting-songswhich-ones) Now it's easy to add music to iTunes once it's put in its new home in your "My Music" folder. If you just keep adding "My Music" as a folder to iTunes (File, Add Folder to Library...) iTunes is smart enough to search that directory and only add songs that weren't already in your iTunes library, so it won't make duplicates of everything in your iTunes playlist (so you can still use iTunes for song rankings and the like). The last part of your question though, that is tricky. Yes, iTunes will put everything in pretty much the order you want...but it's inconsistent, especially for albums that have multiple artists on them, such as soundtracks and compilations. I personally find it annoying that if I have, say, the soundtrack to Beverly Hills Cop there's a 50/50 chance that the songs will all go in one folder, such as: Various Artists\Beverly Hills Cop\The Heat Is On.MP3 Various Artists\Beverly Hills Cop\Emergency.MP3 or each song will be split out by artist putting about 1 song in each of 10 different folders, such as: Glenn Frye\Beverly Hills Cop\The Heat is On.MP3 Oingo Boingo\Beverly Hills Cop\Emergency.MP3 But if you don't want iTunes to do it, how can it be done easily? Well, my recommendation is just spending a little bit of time as you listen to the music sorting it by hand...it's the ONLY sure-fire way to make sure every song is where you want it to be (unless another poster has a silver bullet solution that I have missed) There is another option if you're familiar with a little programming. It would be relatively easy to write a program that would read your MP3's ID3 tags and then move them per your specifications. I wrote a program in Microsoft Excel's VBA that goes through my directory of songs and pulls the ID3 tags into a spreadsheet; it's only three extra lines of code to make that program then copy the songs to a new location based on those ID3 tags. The drawback is that you would have to be very strict to ensure your ID3 tags were correct (and not have some tracks as Glenn Frye some as Glenn Fry and some as Frye, Glenn, etc.) If you're going to put that much work into the ID3 tags it seems just as easy to move the files to where you want them to be. Sorry for the length of this post but I hope it helps.

Also, I do not have Keep iTunes Media folder organized and Copy files to iTunes Media folder when adding to library checked.

http://ask.metafilter.com/148532/More-Efficient-Way-to-Organize-New-MusiciTunesExternal-HD#2127184: Also, I do not have Keep iTunes Media folder organized and Copy files to iTunes Media folder when adding to library checked. This is exactly the problem those features are meant to solve.

Your folder hierarchy is also the way that iTunes would organize your music if you DID have the 'keep organized' box checked. Is the external drive essentially a backup drive? So that you have a complete set of your music on both the external AND PC drives? If so, then letting iTunes organize your music is about all you'd have to do, although you would still have to copy the new files over to the external drive. If that's the part that's tiresome (keeping track of what's new and copying only those files) then some kind of incremental backup software solution may be in order.

You really should let iTunes keep your music library organized. iTunes does an amazingly good job with it. For example, my library has thousands and thousands of songs in it. If I want to find one of those mp3 files in my library, the fastest way is to find it in iTunes and then choose "show in finder" (there might be a different term for it in Windows). But if, for whatever reason, I feel the need to find the file by surfing through my hard drive, iTunes has it filed by artist and then by album. I used to have my own system for filing my music before iTunes came along, and my system worked for a library of a few hundred songs... but once you've got thousands and thousands... it just makes more sense to have a system that automatically files them. iTunes does that for you. Best of all, if you let iTunes file them all for you, you KNOW everything is in the same place. So, if, like me, you decide to create a system for automatically backing up your library, you know everything will be backed up. And I do mean everything. P.S. for any Mac folks who might be reading this. I use http://www.shirt-pocket.com/SuperDuper/SuperDuperDescription.html to back up my stuff and it's been awesome! I have another external drive for Time Machine. I'm pretty OCD about backing up my stuff, especially since external drives are so cheap these days.

Yes, like the others have said - let iTunes organize for you. To make adding music easier, iTunes has an http://lifehacker.com/5356619/itunes-finally-adds-watched-folder-to-automatically-add-new-music folder. Move your music to that folder and iTunes will rename and organize your files, as well as put your music into your library. No more need to manually add music in the program itself.

Arniec, iTunes can organize compilations very easily and efficiently. All you need to do is select "Part of a compilation" on the get info dialog, and iTunes will sort the album folder as Compilations\Album. Or, if it's not a various artists compilation, set the Album Artist field for the tracks and iTunes will sort the album as Artist\Album.

http://ask.metafilter.com/148532/More-Efficient-Way-to-Organize-New-MusiciTunesExternal-HD#2127299: "But if you don't want iTunes to do it, how can it be done easily? Well, my recommendation is just spending a little bit of time as you listen to the music sorting it by hand...it's the ONLY sure-fire way to make sure every song is where you want it to be (unless another poster has a silver bullet solution that I have missed)" Completely agree that in the age of hierarchical filesystems, you'd be a fool to rely on a media library offered by iTunes (or any other application, for that matter). You don't have to sort it by hand though - just use mp3tagstudio, Tag&Rename or similar.