This article assumes you’re switching from another smartphone, like Blackberry, Windows Mobile, or Palm, and are new to the iTunes + iPod (and iPhone!) ecosystem. It also assumes you’re a dedicated Windows user or someone who just recently switched from Windows to the Mac and needs to transfer content to iTunes.

Since longtime iPod (and Mac) aficionados will almost certainly already be using iTunes, your iPhone will sync your existing iTunes content the same as it would any other iPod. And, hey, if you’re a Linux (or any other *nix) user, I figure you’ve kept your content open from the get-go, and already know 18 different ways to get it onto your unlocked, jailbroken iPhone…

Getting iTunes

iTunes is a free download from apple.com and required before you can activate your retail iPhone. (And if your iPhone is unlocked, required before you can easily manage and sync content). If you don’t already have it, go get it now. I’ll wait. Honest.

Making the Most of Your Music

When you’re moving to the iPhone and iTunes ecosystem, the first and easiest content to move over is your digital music (stuff you’ve already bought, ripped from CD, or created yourself).

Moving MP3s and WMAs

First, we have to address the monster in the room — DRM, which technically stands for Digital (Copy) Rights Management, though Draconian Restrictive Measures may be more accurate. It’s a way of locking down content ostensibly to prevent piracy but often to frustrate legitimate users. For now, if you bought music from an online store like MSN Music, Yahoo Music, Zune Marketplace, etc. it’s almost certainly got DRM that will prevent you from easily moving it to iTunes. Don’t worry, I’ll cover ways to work around it (for legitimate purposes only!) at the end of the article.

If your music is already DRM-free you’re good to go and in an iTunes/iPhone supported format like MP3, just drag it over and drop it in (or choose File - Add to Library for you old school menu-lovers). For DRM-free/unprotected WMA (Windows Media Audio, the native format of Windows Media Player) music, while iTunes won’t play it, it will automatically convert it to an iTunes-friendly format for you. (See Ripping CDs, below, for details on how to chose iTunes conversion formats).

I recommend letting iTunes manage your library via Edit - Preferences - Advanced - General - Keep iTunes Music Organized and Copy files to iTunes Music folder when adding to library.

This puts your content into a logical file structure so you can more easily find individual files later with Windows Explorer, avoids wasting space with duplicate content, and prevents iTunes from losing track of something you added (for example off a USB drive) but forgot to copy locally.

Ripping CDs

If your music is on CD, iTunes will rip it straight to either MP3 or AAC (the successor to MP3 which has less support but arguably greater potential quality). Unless you’re tone deaf, I recommend ripping to at least 256 bit. You can set this via Edit - Preferences - Advanced - Importing - Import Using and Setting (Custom).

Buying Music Online

Want to buy music for you iPhone? iTunes is the #1 retailer now and provides nearly effortless browsing and purchasing options. Just hit the iTunes Store link in the sidebar and find what you like. For reason’s we’ll get into in a moment, I heavily recommend buying only iTunes Plus music, which is the higher, 256 bit quality and DRM-free.

Though Apple CEO Steve Jobs has famously said iTunes would rather sell only DRM-free music, currently, EMI and independent labels are the only source of iTunes plus music. Sadly, to try and manipulate and fragment the market, Universal, Sony BMG, and Warner Music will only provide higher-quality, DRM-free music to iTunes competitors like Amazon MP3. But if you live in the US — or when/if they expand the service internationally — Amazon MP3 provides an iTunes friendly, if slightly more challenging to navigate, source for legit iPhone-compatible music.

Doing Your Best With Video

Unlike music, where MP3 is a pseudo-standard, CD ripping is mostly legal, and DRM is increasingly on the way out, video formats are far more fragmented, DVD ripping is mostly verboten, and DRM shows no signs of going anywhere anytime soon.

Moving MP4s, AVIs, WMVs, FLVs, Etc.

If you’ve shot your own videos, DVR’d, or otherwise created or acquired DRM-free video content, it’s only slightly more difficult to move them to iTunes than it is music. The “slightly” part being format. With a wide variety of containers, codecs, and the need to get both audio and video into exactly the right zen-like balance, using something like the free Videora iPhone converter for Windows or iSquint for Mac (or similar application) is almost a must. Open your existing video file, choose the iPhone setting, and let it convert.

Unless you have a fast machine, get a tasty beverage because it will take a while. And make sure you test a sample first, to prevent wasting a lot of time if your settings are off.

Already have, or already converted video content? Drag it into iTunes same as you did your music.

(Note: since iTunes doesn’t store video-type meta data in the video file itself, but rather in the iTunes database, if you want to have movies, TV shows, and music videos all filed in the right place, you’ll have to individually set them in each file’s properties under the Video tab.)

Ripping DVDs

Unlike music, where various “fair use” provisions exist that allow, in many jurisdictions, for you to rip your CDs to your computer, the DVD lobby has succeeded in making DVD ripping illegal in many parts — the reason iTunes doesn’t provide that type of functionality itself.

If, however, you live in a place (or mindset?) that says when you legally buy a movie or TV show on DVD, you should be able to watch it regardless of whether its stays on a disk or moves to your hard drive, then open source software like Handbrake is your best friend. Handbrake will rip most DVDs straight to iPhone format, and add them to iTunes, in just a couple easy steps (navigate to your DVDs video directory, select the iPhone default, and let it rip!).

Bonus tip: make sure, especially when dealing with older movies, full screen movies, or TV shows, that you preview the video and choose de-interlace when necessary to prevent nasty scan-lines from showing up on your digitized video.

Buying Videos

Depending on what country you live in, iTunes provides movie rentals and downloadable movies, music videos, and TV shows. These are DRM-locked (see below) but perfectly compatible with the iPhone. Selection varies greatly from region to region, and some networks — most famously NBC — don’t see eye to eye with Apple’s less anti-consumer model, but until Apple unleashes its own DVR, this is the easiest way to get legit video on your iPhone.

Other Content

Big audio book fan? If you got them from Audible, simply go to Advanced - Authorize Audible Account, input your details, and drag-and-drop your audio books straight into iTunes.

Love podcasts, like our very own Phone Different podcast? Subscribe directly from the iTunes Store (or from the Subscribe via iTunes link from your favorite podcast’s homepage). They’re free, come in audio and video (even HD!) and download straight into iTunes. While you’re there, be sure to check out iTunes University (also under the iTunes Store) for loads of free, and highly educational audio and video, from lectures to speeches to commencement addresses.

Dealing with DRM-Hell

Now for the hard part. If you previously bought music locked down with DRM, especially the more onerous DRM systems like PlaysForSure (or in MSN Music’s case, PlaysNoMore!), there’s a little more work involved.

The Problem With DRM

What’s wrong with DRM? It does nothing to prevent real pirates (many of whom mass-produce content on boats in international waters or distribute online via massive criminal networks) and everything to frustrate regular, legitimate users who just want to upgrade their computers or move their content from one device or room to another.

We’ve all read the stories, from Google Video to Major League Baseball, to MSN Music. People, in good faith, spend their hard-earned money to buy the content they love, only to later get notification that the service they chose, from the vendors they trusted, will no longer “authorize” them to play back that content.

Imagine Tower Records going out of business and some men in black showing up to re-possess all the CDs and LPs (yes, we’re old enough to remember LPs, thank you!) that you ever bought from that store.

Sounds ridiculous, doesn’t it? But with digital content it’s happened before and will happen again. Windows Media Player has also been known to automatically DRM music you rip from your own CDs if you’re not paying attention to the preference settings. So, if you’re stuck with previously bought or ripped DRM music, what can you do?

The Analog Hole

While from time to time DRM-stripping applications show up on the web, most DRM services are bound by their contracts with the big media companies to update the DRM as quickly as possible to render any circumvention obsolete. This makes DRM-stripping unreliable.

A more dependable, although technically “lossy” solution (i.e. some loss of quality will occur, though it will likely be negligible to all but audiophiles), is the infamous “analog hole”.

For music, simply use your old software (e.g. Window Media Player) to burn your DRM-locked WMA (or other format) music to playable CDs, and then use iTunes to rip those CDs back into digital format (preferably MP3).

Voila, the music you paid for, now ready for the device you chose to use it on.

Video is more of a challenge. If you’re an advanced user and have a Media Center PC (or two PCs, depending), with analog output and input, you can try routing your DRM-locked video out and back in, re-recording it like you would a VHS tape or analog cable TV signal. Provided you could then navigate the “black art” of video and audio containers and codecs, using something like the aforementioned Videora, for example, you could convert the captured video into iTunes/iPhone friendly MP4 H.264 format.

Advanced Capture

Even more advanced users willing to brave challenges like hardware acceleration and video layers? Capture software like CamStudio might let you avoid the digital-analog-digital loop. Your mileage, however — and frustration level — will vary.

An Ounce of Prevention

While Apple has among the most progressive DRM systems on the market, with the ability to sync any number of iPods to your iTunes, and authorize up to 5 computers to play your DRM-locked content (and the ability to call Apple for one-time re-downloads and re-authorizations should something go wrong), it’s vital to remember to BACK UP you iTunes content. USB hard drives are now ridiculously cheap and ridiculously big, so get one and copy everything to it, and update the copy regularly.

Also, burn playable CDs of all DRM-locked music and rip them back into iTunes so that, in case of system loss, re-install, or other catastrophic problems, you don’t have to worry about getting locked out of your own music.

Conclusion

Well, there they are, my tips and tricks for getting your content off the old and outdated and onto iTunes just in time for your brand new iPhone. But try as I might, I know our readers — the real content ninjas — have a whole host of sneaky black magic all their own.

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