iPhone sync tricks

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Apple’s view of the environment that the iPod, iPhone, iTunes, and Apple TV live in is a simple one. Not that people at Apple don’t understand that many of us media consumers aren’t crazed power-users with gig after gig of media stashed all over the place — after all, if you hold down the Option key when you launch iTunes, you’ll get the choice of switching to an alternate iTunes library, and that’s as power-usery as a feature can be.

But quite rightly, the people behind Apple’s iTunes ecosystem have designed iTunes to appeal to the vast majority of people with the simplest of all set-ups: one computer with all your stuff on it. I don’t dispute that this is by far the most common set-up out there, but the work Apple does to make life easy for the most common user types can make things downright difficult for the rest of us.

I learned this lesson when Apple added music sharing to iTunes. I use a laptop as my primary system. Rather than clutter up my laptop’s hard drive with duplicate music files, I sync my full-sized iPod with the Mac at my house that contains my entire music collection, and then plug in the iPod in order to listen to that music when I’m at work. But it turns out that while you can play music directly from an iPod (thanks for not crippling that feature yet, Apple), you can’t share the contents of an iPod with others. Nor can you use the vaunted Party Shuffle feature. Oh well. I learned to live with the disappointment.

But with the iPhone things have gotten a bit stickier. The iPhone, like the Apple TV before it, won’t do anything but sync. You’ve always been able to pop an iPod out of sync and into “manual mode” and just drag media files onto it (and delete files off of it) at will — but the iPhone and Apple TV must sync. There’s no “manual mode” for those devices.

Music here, photos there

While auto-syncing can be a fantastic feature, it can also be infuriating. As I write this, I’m sitting at work. On my desktop is an MP3 file I downloaded today that I’d like to listen to on my way home, on my iPhone. But I can’t — not without erasing the entire music and video contents of that phone. That’s because my iPhone’s music and video libraries are synced to my home Mac.

But here’s the funny thing: if I can find that MP3 file as a podcast, I can add it to my iPhone. That’s because my iPhone is currently attached to three different Macs, syncing different types of data with each of them. It syncs contacts, calendar data, and podcasts with my laptop. It syncs music and videos with my home media-server Mac. And it syncs photos with my home Power Mac G5, which is where all my photos live.

Yes, it’s true — the iPhone is a sync-only device, but it’s a flexible syncer. Apple seems to have broken iPhone data into discrete blocks, each of which can be synced with a different computer: Info (contacts, calendars, bookmarks, mail accounts), Music and Video (which must be synced together), Photos, and Podcasts.

The playlist workaround

Now, about that sync-only thing. The good news is, there are workarounds that can give you some control. The easiest trick is to create a playlist in iTunes and set that playlist to auto-sync. For both my Apple TV and my iPhone, I’ve got playlists that are dedicated to video for those two devices. This lets me manually control what videos appear on my iPhone (important since it’s got a limited amount of storage space) and my Apple TV (which has massive storage compared to my iPhone, but would choke if it tried to store all the videos in my iTunes library). If I want to add a video to those devices, I drag them into their respective playlists. If I’m done watching a video, I select the playlist and delete it.

It’s not quite as immediate as adding or deleting the file on the device itself, but it works pretty well. There are some quirks, though. For one, although the iPhone kindly offers to delete videos after you’ve watched them, the next time I connect my iPhone for syncing that video gets copied right back, because it’s still in the playlist.

Syncing with Smart Playlists would be a great workaround for hands-on video management on these devices, but there are some quirks there, too. Here’s an example: let’s say I want to populate and Apple TV or iPhone with a combination of TV shows. For some shows, I only want the most recent unviewed episodes. For other shows, I want to hand-pick which episodes I want to load.

iTunes’s video syncing feature lets you sync all, the X most recent, or the X most recent unwatched videos, either globally or for selected playlists or shows. But you can’t mix and match — either you’re syncing unwatched shows, or all shows, or recent shows, in every playlist.

You’d think making smart playlists would be the workaround. In theory, I could set up one playlist with handpicked videos, but set up another playlist to display all unwatched episodes of a particular show or shows. And here’s where the quirk comes in: although iTunes understands the concept of a “watched” TV show or movie, Smart Playlists don’t. Oh well.

( Update: Thanks to the brilliant readers of Macworld who pointed out that the blue "unwatched" dot in iTunes is essentially a hack representing a video with no data in its Play Count field. So this trick will work: Make a playlist [smart or otherwise] filled with the shows you want to watch; then make a Smart Playlist with two conditions: Playlist is [name of your previous playlist] and Play Count is Less Than 1. And presto -- an auto-updating playlist that will replicate the behavior of iTunes' "unwatched videos" setting without forcing you to only sync unwatched videos to your device.)

Syncing calendars

The iPhone has made a lot of people reconsider using Apple’s iCal, since that’s the Mac calendar program that the iPhone syncs with out of the box. The thing about iCal is — at least until Leopard arrives — it’s kind of a dumb calendar. You can share calendars with other people, yes, but it’s a read-only kind of thing. Which brings us to a question sent in by iPhone Central reader Mark Fawcett:

I bought my wife an iPhone… she currently syncs her iPhone with the Address Book and iCal on her 17” MacBook Pro, but she also has a secretary who needs to add appointments and meetings on the secretary computer’s calendar and then sync them with my wife’s iPhone. While my wife’s computer is a Mac and uses Address Book, iCal, etc., the secretary’s computer is a Windows PC. What can we do to make sure that the sync’ing all works out.

This is a similar situation to the one I’ve got — the only difference being that I don’t have an assistant! But I’ve got two calendars, one for work and one for personal stuff. And I found that my wife was always asking me to put items on my calendar or change existing items, as our personal plans changed. I wanted to find a way for her to edit my iCal calendar, while also letting me edit it.

The answer: Spanning Sync, available for $25 a year or $65 for a one-time purchase. Spanning Sync is a delightfully clever utility that syncs iCal calendars with Google Calendar. Not one-way syncing, either — Spanning Sync is a full two-way sync. In Mark’s scenario, his wife can continue to update her calendar on her Mac using iCal. But her assistant can log in to Google Calendar and create and edit events on that same calendar. Spanning Sync will make sure that the two calendars are kept in sync, with updates as often as once an hour.

It’s worked for me — every so often new events magically pop up on my personal calendar, left there by my wife. And they automatically sync to my iPhone. Now that’s how it’s supposed to work!

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