I like my iPhone and iPod but I am no Apple fanboy. After upgrading to iOS5 and trying to use iCloud yesterday and migrating these devices to a new PC 10 days ago, I am frustrated and have lost a lot of time. 

I’ll start with a condensed narrative of my woes, then draw my conclusion.

The upgrade to iOS5, Apple’s latest operating system for iPhones and iPads, was bumpy. I saw a lot of chatter on the web that many people had problems. In the end, my upgrade worked but the prompts along the way were confusing.

Even more confusing was iCloud, which allows synchronizing contacts, calendars, and other information automatically across i-devices and a PCs or Macs. A blow-by-blow explanation would bore so I point you to Outlook 2010 PC? It’s iCloud Or Google Calendar Sync, Not Both – And Outlook 2011 Mac Gets No Love, a blog post by noted techie / search engine expert Danny Sullivan.

Sadly, I was not able to find any helpful Apple documentation; I had to rely on web searches and hits like the one cited. Along the way, I noticed that in iTunes (the synchronization software), under Help, iTunes Help, I received a “Not Found – The requested URL /itunes/win/10.5/ was not found on this server” error. Huh? This was a freshly updated iTunes.

I had a similar experience 10 days. Once I lost my job, I had to migrate my two i-devices from the company computer to my own. I spent hours in advance trying to figure out how best to do so. My search of the Apple support site for what I thought must surely exist- the one-page, step-by-step guide for this task – yielded nothing very helpful. After consulting web resources, I thought I had it figured it out. I confirmed with a call to Apple support (my iPad is still in the free support period). My plan worked but I panicked initially because I thought all my apps disappeared. Then I realized iTunes had moved all the apps several i-device screens over to the right. Aside from the time to re-organize my apps, no where did I see a warning this would happen.

Running into these problems was a huge waste of time. The conclusion? Either the technology has to be so truly simple that no documentation is required. Or the developer has to acknowledge some complexity and provide adequate documentation. Documentation does not appear to be Apple’s strong suit. There is no question the iPhone and iPad are beautifully designed and wonderful machines. Yet they do entail some complexity. Complexity that Apple appears to ignore.

On and off, I consider switching from a PC to a Mac. After this experience, I am reluctant. With a Mac, I doubt it would be long before I ran into a tech glitch and struggled to find answers.

Law firm CIOs try to keep tech easy but know simplicity is not always possible. That’s why firms train and provide ample support. A BigLaw CIO who took Apple’s approach to complexity (seemingly ignore it) would likely not last long!