Information In The Cloud: Freeing My PIM (And Other) Data From Its Microsoft Shroud

Last Friday and Saturday, I took my new-to-me wheels on their first serious road trip; a long-distance but short-duration visit to Silicon Valley (the wheels passed with flying colors, by the way). I was pretty exhausted on Sunday, with barely enough energy to keep my eyes open, press my fingertips down on MacBook Air keys, and fire up a few brain cells. Therefore, I decided to tackle a project I’d long been pondering and planning: freeing my personal data from its virtualized Windows XP ‘prison’, ideally without incurring incremental one-time and/or subscription fees in the process.

My work’s unfortunately not yet done, due to service limitations, but I’ve learned a lot (and picked up a few fresh scars, to boot) in the past few days. While the premise of ‘cloud’-based storage is alluring, as is my to-date extreme pleasure with Firefox bookmark synchronization, the ‘devil’s in the details’ as the saying goes. And if my experience is indicative, it suggests that reality is still fairly demonic…and it shows just how challenging server-and-multi-client sync can be to implement in a feature-rich and robust fashion that customers expect. Read on for the sordid particulars.

In the early days of my EDN career, mine was an all-Windows shop. Nowadays, however, my home-based office contains a mix of Apple- and Microsoft-fueled desktop and portable systems. I also regularly use an OS X-based iPod touch to check email and peruse websites, as a successor to my Linux-powered Nokia N800 Internet Tablet. To date, I haven’t strayed from the series of Windows Mobile-based cellular phones that I’ve sequentially used in recent years, but USB-tethering them to a computer in order to sync PIM data was always a pain, and it can be a hit-and-miss proposition in a virtualized hardware environment. Plus, I’m tempted by the SIM-unlocked RIM/AT&T BlackBerry Bold 9000 that just arrived for testing, although its lack of 1700 MHz support means I won’t be able to tap into T-Mobile’s 3G data services (then again, I can’t access UMTS on my current T-Mobile Dash, either…).

As my stable of communications-and-computing hardware diversifies, I’ve found myself feeling increasingly frustrated with only being able to access my calendar, contacts and to-dos through virtualized Outlook 2000 running on a single laptop PC, one hard drive crash away from obliteration. Similarly, my ASCII text file-based list of what bills to pay (and when, and how much is due), books to read, music to listen to and movies to watch was stored on the virtualized HDD of that same MacBook Air. Sunday morning, I decided it was finally time to put my data in the ‘cloud’, privacy concerns be damned. And, after considering numerous ‘cloud’ storage startup companies whose long-term prospects were by no means guaranteed, along with Microsoft’s various Live services (which I primarily discarded out of principal; wasn’t the point to get away from a Windows lock?), I settled on Google as my hosting effort beneficiary.

The ASCII file contents ended up being the easiest information to migrate. A simple copy-and-paste turned it into a Google Docs document, and after I installed the Google Gears browser add-on, I also gained offline access to my lists. The biggest question I’ve got about Gears, which Google searching (irony intended) hasn’t answered, involves conflict resolution. Say, for example, I create a local cache of the same file on two different computers, then edit both copies offline. What happens when both computers subsequently go back online, either sequentially or at the same time; which version(s) of the file will Google Docs pull back up to the server?

Outlook 2000’s Tasks list, conversely, has so far remained mired in its original location. Google doesn’t (yet) provide any sort of migration or sync utility to get this particular Outlook data up to its servers, and anyway the company’s online Tasks applet (which recently gained direct mobile browser access capability) is woefully under-featured in comparison to Outlook’s version. Then again, it’s only a Labs project at the moment, so there’s hope for future improvement. And although (as you’ll soon read) I found a way to get other Outlook data to Apple’s OS X-inclusive PIM applications, Outlook Tasks-to-iCal To Do migration isn’t supported by Apple’s translation tool.

It was critical that my list of nearly 3,000 contacts’ details survive their migration to Google Contacts as intact as possible. Conversely I could if necessary re-enter relevant calendar information from scratch at the Google Calendar (which, by the way, is not yet Gears-enabled for me) destination. So I focused my initial attention on the Outlook Contacts data transport; subsequent sync was a secondary concern. Online documentation from Microsoft suggested that it’d be possible for me to accomplish this objective by exporting the information as a CSV (comma separated value) file. Yet Google Contacts refused to accept either DOS- or Windows-formatted CSV variants, returning a ‘failed with unknown error’ message at both import attempts. A program called OggSync also claims to handle Outlook-to-Google contact and other data migrations, and v4’s embrace of the Google Contacts API further increased my confidence. But the free version of the program doesn’t support Contacts transfers, and I wasn’t up for dropping $29.95 on a year’s subscription with no in-hand proof that the program delivered on its promises.

I did, however, have an active .Mac (now called MobileMe) membership, so I decided to use OS 10.5’s Address Book as an intermediary between Outlook and Google Contacts. The MobileMe sync utility requires two things on the Windows side of the to-server bridge:

• An installed copy of iTunes (although, as I discovered, it wasn’t necessary to activate the software with an iTunes Store account or even to launch it for the first time), and
• Outlook 2003 or 2007.

A comment on MobileMe before continuing: it’s commonly described as being a ‘$100/year’ service and indeed that’s true, but only if you buy it from Apple (where, technically, it’s only $99). Get it from Amazon or another large online merchant, on the other hand, and you’ll only pay $69.99 or so; it’s even cheaper when it’s on sale.

Continue reading with Part Two of this series, ‘Information In the Cloud: Contacts Quagmires‘…