Organize your PDF library with iTunes

Yes, I know iTunes isn't a document organizer, but it does a surprisingly good job at it anyway. Using iTunes' Smart Playlists and its PDF support, you can build a document library where PDF's are automatically sorted into keyword-based lists. Let's get started.

What you'll need to digitize your documents as PDF's

   1. A scanner. Document scanners are small, sleek and super cheap these days - some as low as 50 bucks - so pick one up to digitize dead tree material like newspapers, magazines, or paper receipts. Your scanner software will most likely provide an option to output the scan to a PDF document. If you're going to digitize stacks of paper at once, you'll want one equipped an auto sheet feeder. (Hardware's not my forte, and the model you get depends on your needs and budget - but this thread has some recommendations from your fellow readers.)
   2. A print-to-PDF program. Windows users should download the free CutePDF writer for the ability to print office documents, email messages, images and web pages to a PDF file. (Seriously, CutePDF is a must-have.) Mac users, printing to PDF is all built into to OS X, so you don't need to do a thing, except choose PDF from the print dialog.

Create a separate iTunes library for your documents

Strange bedfellows, your 1099's and those Beck MP3's, so you'll want to create a whole new "all business" iTunes library for your PDF's. To do so, hold down the Shift key when you launch iTunes (Option for Mac users), and hit the Create Library button from this dialog:

Give your document library a serious name - like "PDFDocuments"

Once you've got a new library set up, you can drag and drop PDF's onto it to add them. But before you do, a couple of tips for dealing with PDF's in iTunes:

    * By default, when you add PDF's to your iTunes library, iTunes copies them into the folder where it keeps its data, leaving you with two copies of the document on your hard drive. It also creates artist and album subfolders, which don't apply to your PDF's (they'll all be "Unknown Artist" and "Unknown Album.") To keep your PDF where you originally stored it, in the iTunes Preferences pane, the Advanced tab, uncheck "Copy files to iTunes Music Folder when adding to library" and "Keep iTunes Music folder organized."

    * Remove all the music-specific fields from the default listing, like Artist, Album, and Last Played by right-clicking on the column header and unchecking them:

Develop your tag vocabulary and create Smart Playlists

Once you've added a few PDF's to your iTunes library, you want to organize them into virtual folders - actual playlists. The advantage playlists have over folders is that one document can live in more than one playlist - so that 1099 form from 2006 can live in the taxes list, the 2006 list, the income list, and the 1099 list.

You could manually create playlists and drag and drop your PDF's into them. Even better, you can use Smart Playlists that dynamically populate based on keywords. For example, I renamed the PHP Manual PDF "PHP Manual (ebook code)" then created a Smart Playlist for ebooks, all PDF's where name contains the word "ebook":