My encounters with Apple’s attempts to deliver a reliable online service have been decidedly mixed. Although most of you probably believe that it all began with iTools, a free set of online features, including email, which debuted in 2000, Apple’s shaky online service history goes back further.

Indeed, the progenitor of MobileMe — and now iCloud — wasn’t Apple’s first attempt at taking their customers online. Back in the 1980s, Apple had an online service for dealers, AppleLink. A small startup company, Quantum Computer Services, made a deal with Apple to create a Personal Edition version of AppleLink, which would deliver a similar online service to consumers.

When the deal fell apart, Quantum decided to roll their own, and rebranded the service America Online — later renamed AOL when it expanded beyond the boundaries of the U.S. But they continued to follow the Apple mantra, which was to make the service easy for regular people to master and get online, at the expense of making it too simple according to some skeptics, who also complained about AOL’s infamous walled garden.

But AOL used a clever marketing scheme right out of the starting gate, sending millions of setup floppies to potential users. They also undercut the other players in the online business on price. AOL had a flat $4.00 per hour rate, which later morphed into a flat rate as other services began to try to beat them at their own game.

In the 1990s, AOL and Apple got together for eWorld, which was basically a version of AOL with an Apple-inspired interface. It bombed, and Apple stayed out of the online business until iTools arrived. But the ups and downs of AOL aren’t part of this story.

Beginning with iTunes, Apple’s resurrected online service has embarked upon a long and shaky journey, and the outcome may not at all be certain to this very day. Free became paid in 2002, and iTools was rebranded as MobileMe in 2008. But over the years, basic features remained flaky. There were periodic email outages, and other services didn’t always work as planned. Indeed, the MobileMe launch was so bug-ridden that that Apple staffers were given a dressing down by Steve Jobs at a special corporate meeting.

Segue to 2011, when MobileMe’s end was announced. Henceforth there would be iCloud, basically a scheme to store your Apple-related stuff on their massive server networks. MobileMe fades out as of June 30, 2012, meaning that a few features will go away. But email and the ability to sync some of your stuff, such as contacts and bookmarks, will remain a part of iCloud, assuming the system works. Just this week, Apple began to offer free DVDs of OS X Snow Leopard to help entice more Mac users to upgrade to Lion, and set up iCloud.

But that’s where things get dicey, to put it mildly. The arrival of iCloud has involved a fair amount of glitches. As I write this story, some 1% of iCloud users, according to Apple, have encountered various email outages. My former MobileMe email was part of that list, though the situation has improved. Then again, Google’s Gmail had an outage too this week, so let’s not center all the blame on Apple. It’s clear that cloud-based systems are still works in progress.

That said, my personal experiences with iCloud haven’t been so good even when you take email out of the picture. The same can be said about a related service, iTunes Match, which uses Apple’s massive music library to allow you to put up to 25,000 of your songs in the cloud for a $24.99 annual fee.

With iCloud, my biggest problem is syncing. I want my contacts to be the same on my Macs, an iPhone 4s, and a third generation iPad, but that remains an unfilled dream.

On my main desktop computer, a late 2009 27-inch iMac, Address Book will often list a contact at least twice — some users report over a dozen listings for some of their contacts. Worse, when I try to remove one of the duplicated contacts, it will, ghostlike, reappear just seconds later. I’ve kidded about the phenomenon on my tech show, since I also host a radio show about the paranormal. But it’s obviously Apple’s screw up to fix, and it’s unfortunate that iCloud, although a key to Apple’s future success, is so bug-ridden.

Another problem, with iTunes Match, is the inability to properly match your own music library, ripped from regular CDs and elsewhere, with the corresponding tracks in Apple’s library. I’ve reported about this problem before. Most tunes match, some don’t, and it doesn’t seem as if the ongoing updates to iTunes, which claim fixes to iTunes Match too, have addressed the fundamental problem, or that Apple will even admit to what’s wrong.

The problem for Apple now is that they don’t have an awful lot of time to fix iCloud. Sure, Apple’s products are amazingly popular, and you are thrust into the iCloud environment almost by default as you set up a new piece of equipment. At the same time, Microsoft and Google have their own fledgling cloud services, not to mention Amazon and other companies. Yes, there may be 100 million iCloud users, but it doesn’t mean that they are going to tolerate ongoing email problems and various and sundry glitches for long before they log out forever. Since a great part of Apple’s walled garden — or integrated ecosystem — depends on iCloud working reliably, I wonder how much time they really have to set things right.

Meantime, I’m happy to make a pitch once again for some way for Apple to allow you to combine your various Apple IDs. I’ve heard that they may already be doing this on occasion, and I really have only two names to merge, so maybe I’ll see if I can get a favorable response. Maybe the answer is for every one of my readers — and feel free to tweet the message — and loads of other Apple customers to complain and request that Apple combine their Apple IDs to help ease the iCloud transition. Apple may even listen, even if they need a few million wakeup calls to show them the way.

This article was posted on Friday, April 20th, 2012 at 12:00 AM and is filed under News and tagged with: Amazon, America Online, Aol, Apple, AppleLink, cloud services, eWorld, Google, iCloud, Iphone, iTools, Itunes, iTunes Match, Mac Os X, Microsoft, MobileMe, snow leopard, Steve Jobs.