Since iTools burst onto the scene at MacWorld Expo 2000, Apple has cultivated its once-free online service into a powerful, push-friendly suite, albeit one saddled with increasingly uninspired names and clunky roll-outs. The latest iteration, MobileMe, stumbled onto the scene alongside iPhone 3G promising a “simple way to keep everything in sync,” but instead delivered a series of outages, half-truths, error messages and, eventually, an apology.

Now that that’s all behind us, of course, MobileMe works nearly as well as Steve said it would. But getting there felt more like a drive through Redmond than Cupertino — and that’s after Apple plugged up all the holes:

Push It Kinda Good
After Steve Jobs’ flawless WWDC demo, we .Mac users had no reason to think the pushy successor wouldn’t have Apple’s legendary ease of use. So, as soon as Me.com went live and iPhone 2.0 popped up in iTunes, I naturally assumed Apple’s trademark out-of-the-box functionality would quickly follow.

So I updated my iPhone, slid over to System Preferences and turned on Push, and waited for the magical .Mac transition to happen.

Not exactly. E-mails I test-sent to myself didn’t quite show up instantaneously, and my brand new Contacts app didn’t quite sync so well (or at all) with the test cards I made on my Mac. So, I sauntered over to Software Update on my PowerBook and installed the OS X Update for MobileMe, which replaced all of Leopard’s .Mac references, but still left me unsynced and unfulfilled.

Since time was of the essence, it being a Friday morning and all, I left my MobileMe cloud looking a lot like a question mark.

(On my way to work, I downloaded MLB At Bat from the App Store while sitting in traffic — funny how a few in-game highlights can make you forgot your troubles. Later, I read all about Apple’s launch woes on the New York Times app, and figured there wasn’t much I could do to help my cause. Besides, I had Mahjong and Aurora Feint to play.)

MobileMeltdown
Two and a half days later, I returned my iPhone to its sync cradle and hoped for the best — mind you, I’m not really sure what I was hoping for, since I was fairly sure that push e-mail was working by this point and had all but given up on Contacts. The ones I added on my iPhone stayed on my iPhone and, frankly, I was just fine with that.

After a restore, I tinkered around in iTunes a bit — switched up some of my music, added a few playlists, deleted a ringtone or two, and ... hello, what’s this? Under the Info tab, the sync checkboxes for Contacts, Calendar and Bookmarks were all apparently unchecked, meaning, of course, that no amount of tinkering, wishing or hoping would make anything sync, least of all my contacts, calendars and bookmarks. So I promptly checked them all and re-clicked the Sync button.

Eject. Slide. Tap.

Back to System Preferences on the iPhone to change the Contacts, Calendars and Bookmarks switches to On, On and On. (A note here: I didn’t actually want to sync my bookmarks, as the set of favorites I had accumulated on my iPhone were entirely different than the ones on my Mac, but I suppose I got caught up in the moment.)

A scary message appeared Existing contacts will be removed from your iPhone — accompanied by an ominous red Sync button, which I pressed.

As my finger tapped the button, a wave of anxiety washed over me, not unlike the one I felt when the stupid-looking flying duck used to appear on my old IBM ThinkPad. It was a strange, foreboding feeling that I hadn’t really felt since I slid my first Made in Cupertino product out of its box.

Back to the home screen, I opened the Contacts app just in time to see all of my numbers and addresses disappear...

Just a slide to the right
Like most every iPhone owner, all of my newest contacts are stored on my handset, many of which are rather important. So, seeing them all vanish — despite having backed up my phone just moments ago — was a tad disheartening. It took about 9 of the longest seconds of my life for them to reappear, but when they came back, my relief was fleeting; upon scrolling to the most recent contact I remembered adding, there was no trace of him.

As Doc Emmett Brown would say: “Erased ... from existence!”

Frantically, I plugged my phone back into my computer, unchecked the Contacts box and again synced everything back to my MobileMe cloud, crossing my fingers and rubbing my imaginary rabbit’s foot.

(Perhaps I should explain myself for a moment. Despite my frenzy, I was, at no point during this terrific ordeal, worried that Apple would hand me my first horror story. Syncs and all, this whole scene lasted about 13 minutes and 19 seconds, not nearly enough time for panic to truly set in, at least not for a seasoned Mac user.)

Back at the Contacts app, which had once again gone blank, I watched the spinning circle do its thing until the list of names reappeared, and viola! Numbers, e-mails and addresses were back in their right place, and I was comfortably back at Square One.

I sauntered over to my iMac and opened up System Preferences. Everything was all hunky-dory with my account in the MobileMe pane, so I pressed Sync there, too, upon which a familiar .Mac question about merging or replacing data (which seemed a bit too risky at this juncture) was posed.

A moment later, my Mac’s Address Book was overflowing with an assortment of names from my iPhone, and I exhaled.

Slide. Tap. Tap. Slide. Tap. Tap. Whew!

It wasn’t a bug, Mike
As it turns out, Apple anticipated every one of my missteps in a handy Web posting called MobileMe Setup. With step-by-step instructions for Macs, PCs and iPhones on either platform, Apple took away the guesswork and need for columns like these.

I guess I’ve just been spoiled all these years. Because I never thought to look.

While Apple’s directions would have saved me a few hours of indigestion, my journey helped me understand exactly what MobileMe does and doesn’t do: For one, push e-mail doesn’t extend to sorting of e-mail messages. New messages are received instantaneously on my iPhone, but if I delete, junk or store them on my Mac, I need to manually refresh all my other inboxes before the changes appear.

Of course, the push limitations on the Mac are well-documented, and ultimately, the woes I experienced can be traced to the 15-minute lag between data hook-ups; had MobileMe properly pushed my Contacts data to all my devices as advertised, my iPhone adds would have showed upon initially unplugging my iPhone, since they were clearly cloud-bound all along.

That being said, it hasn’t been a problem since, and it’s doubtful I’ll ever be bothered by it again. And aside from a pesky glitch that keeps telling me “MobileMe will change more than 5% of your Mail Accounts on this computer,” and an annoying flaw that sometimes pushes the same message twice to my iPhone, Apple’s new set of Internet tools is a vast improvement over .Mac and makes iTools look like child’s play.

And so what if it I erased a year’s worth of Phone bookmarks?