It should be a stress-free ascent, but our Apple guru finds himself confronted with all kinds of complications when moving to the Cloud...
A confession: for some time now I have been spending my time between two operating systems. While waiting for Lion to mature from a newborn cub to the adolescence of 10.7.2 (brimming with the enthusiasm of youth, occasionally petulant but, contrary to type, happy to wake from sleep on demand!), I have been keeping a venerable install of 10.6.8 going for day-to-day administration tasks and using Pro Tools 9.
However, now that Pro Tools 10 is fully qualified with Lion, I'm moving on and, as part of that transition, I decided to embrace iCloud and all that it has to offer. For newcomers to Macs, the process of setting up hardware and an Apple ID for the first time is designed to be blissfully simple. But for the rest of us, moving a legacy of multiple Apple IDs, mail accounts and personalised workflows raises a few issues.
I have (or had) a MobileMe account and a second Apple ID (a non-Apple email address) that I use for iTunes Store purchases. I could have associated either with iCloud (or even set up a new Apple ID), but I decided to go with the MobileMe account, as that would give me 25GB of cloud storage (until next June) instead of the usual 5GB. For MobileMe users, transitioning to iCloud needs to be activated at www.me.com/move.
Plenty of warnings are offered during the process, and rightly so. The iDisk, iWeb and Galleries functions are not supported by iCloud, but will continue to function until next June; plenty of time to forget to back up all that critical data you spent hours uploading to the world's slowest online storage solution! For Calendars and Contacts, you are advised to back up before making the transition. Don't ignore this advice: in my case, Calendars moved to iCloud without a hitch, but Contacts did not, so having the archive to hand was a lifesaver! You can back up both iCal and Address Book by going to File / Export and selecting the relevant option.
For the Mail app, it's always worth archiving mailboxes as part of a backup routine. Be aware, however, that MobileMe mailboxes set up in Snow Leopard's Mail app will stop working after transition and, no matter what you read on discussion groups about resetting passwords and recreating mailboxes, you will not regain their functionality. Other mailboxes for POP3 and Exchange accounts remain unaffected.
One reason you may feel the need to switch to iCal is to access iTunes In The Cloud and iTunes Match. As this is a common source of confusion, let me clarify that iTunes In The Cloud is a service that is independent of iCloud, and is activated on a Mac by signing into iTunes with the Apple ID that you use for iTunes purchases. You can use the same ID on iOS devices by going to Settings / Store. On the Mac, this allows you to download previous purchases (music, apps and books) by choosing 'Purchased' from the Quick Links on the right of the iTunes Store homepage.
In order to download all previous purchases, select one of them from the list and the 'Download All' button will appear at the bottom of the page. To enable automatic downloads of purchases made on other devices, go to iTunes / Preferences / Store. On an iOS device associated with that Mac, automatic downloads are activated in Settings / Store. Non-iTunes purchases can be accessed by syn'cing — no change there, then — but this can now be achieved wirelessly by going to Settings / General / iTunes WiFi Sync.
The service I was hoping to access was iTunes Match, in order to legitimise my music collection by paying an annual subscription — sorry, what I meant was: obtain high-quality, non-DRM AAC versions of all the music I have transferred to my iPad from CDs I own, in order that I can then stream those tracks on demand to all my other devices — but I can't tell you very much about this yet, as it is only available in the US at the time of writing, and this situation may persist well into the new year. The same goes for volume licensing when purchasing multiple copies of iOS apps!