Buying an iPod is easy. Filling it with video turns out to be much more difficult.

Apple Computer’s iTunes store, of course, offers a few TV downloads for purchase at $1.99 each. Those include a smattering of shows from NBC, USA Network and the Sci-Fi Channel.

The selections are likely to improve, just as the iTunes lineup has gradually expanded to include additions like the Grateful Dead.

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But that won’t help anyone who owns a video iPod today and wants to watch something beyond "Lost" or "Desperate Housewives." It especially won’t help someone with a library of DVDs that would make perfect iPod fodder.

Some products announced at the Macworld 2006 conference here this week try to make this task easier.

Elgato Systems’ new EyeTV 2 is a visually appealing upgrade to the company’s TV tuning software. It requires that you have one of Elgato’s external USB or Firewire-connected tuners. (They’re Mac-specific, but plenty of Windows equivalents, such as the Cats Eye USB HDTV tuner and MyTV ToGo, exist.)

After plugging the $350 EyeTV 500 box into my Apple PowerBook, I could select which broadcast TV programs I wanted to watch. The EyeTV 500 receives only digital signals, which yielded about a dozen channels in downtown San Francisco. The software is straightforward, and the reworked layout now resembles iTunes: Click on a program name to record, then manage saved recordings in playlists.

All that was painless enough. The problem came when translating my saved high-resolution TV shows to the lower-resolution, typically 320x240 pixel format that works best on the iPod.

On an 18-month-old PowerBook with a 1.3GHz G4 processor and 512MB of RAM, the process was painfully slow. Converting a 1920x1080 version of a single episode of "Malcolm in the Middle" took more than three hours. The poor little laptop just wasn’t up to the task.

The good news is that once the conversion was finished, the show automatically popped up in iTunes. And it’s possible to set an option to convert TV programs as soon as they’re recorded, which means the process takes place in the background—as long as you don’t mind waiting.

The copyright law obstacle But my fiancee and I have relatively few TV shows recorded, and we have far more DVDs. Because we’re flying from San Francisco to Ft. Lauderdale, Fla., later this month, I wanted to transfer some of her "Sex and the City" episodes to an iPod.

Unfortunately, the software to do so isn’t legal to distribute in or import into the U.S., thanks to the Digital Millennium Copyright Act. Section 1201 of the law bans software designed for "circumventing a technological measure"—in this case, the CSS, a copy-protection algorithm in commercial DVDs.

That’s led to a bizarre legal result. Because of a twist in the law, the software to move DVDs onto a video iPod is illegal to sell but probably legal to use—if you can get it.

"You’re permitted to do it, but nobody’s permitted to help you," says Peter Jaszi, who teaches copyright law at American University in Washington D.C.. "And you’re not permitted to help anyone else." (Although, Jaszi cautions, that’s "not a perfect argument" because it relies on a legal theory that hasn’t been tested in the courts.)

Fortunately, the DMCA doesn’t apply internationally. I found Macintosh OS X software called HandBrake that’s available from a server in France. (Windows users have options like DVDx and DVDDecrypter.)

HandBrake turned out to be almost as straightforward as EyeTV 2. After scanning a DVD, it lets you choose which titles to save (movies tend to have one long title, while TV shows have multiple). On a PowerBook G4 with a 1.67GHz processor and 1GB of RAM, ripping a 48-minute TV show took about two hours.

The wait was worth it. At 320x240 pixels, DVDs look stunning on the iPod’s screen, and a 48-minute TV segment took up 300MB. That means about 20 shows can be squeezed onto a 60GB iPod—far more "Sex and the City" episodes that anyone really needs.

The Usenet option The problem with both of these techniques—over-the-air TV and DVD conversion—is that they’re slothful. Waiting for a video file to be converted on a computer that’s not top-of-the-line feels like a throwback to the 1980s, when BBS users waited hours for an 800KB file to be sucked through a modem’s tiny pipe.

One solution is to download pre-converted files already in the iPod’s relatively low resolution. File-swapping networks are one way to do this, but for those people worried about ending up on at the business end of a lawsuit, there’s Guba.

Guba is a Web-based front end to Usenet, optimized for unlimited downloads of TV shows for a $15 monthly fee. At Macworld, the company announced an RSS feed that alerts customers to when new video are posted that match keywords they specify. (Guba says that, for copyright reasons, it "does not index feature-length films or MP3s.")

The catch, though, is that the video quality depends on the person who uploaded the show in the first place. An episode of "Alias" that I randomly selected turned out to be 384x208 in resolution and 77MB in size. Although downloading was speedy, the quality was fair to middling compared with my manually converted 300MB shows from a DVD.

Many shows are limited. A search for "Buffy the Vampire Slayer" turned up 14 episodes, some of them duplicates and four mischaracterized. The "Star Trek" newsgroup, on the other hand, featured 103 videos. As you might expect from Usenet, pornography is disproportionately represented.

One handy option that Guba now offers is an "iPod download" feature. I tried it with the "Buffy" episode called "Wrecked" and it worked flawlessly, converting a larger AVI file into a 320x178 MPEG 4 movie that took up 106MB. It was probably converted from a DVD because it had no advertisements.

These video-to-iPod techniques do work, but they’re needlessly complicated and irksome. So why aren’t thousands of shows available for $1.99 through iTunes?

Most movies and many TV shows are already on DVDs, so the hard work of digitization has already been done. Now it should be just question of Hollywood realizing that it’s in their business interest to cooperate and increase their revenue. Until then, I guess, there’s always Guba.