This is a topic of great interest to me. I've evaluated a similar setup.

I've run into two issues:

1. It's a termination offense to sync my corporate outlook calendar with an external server. Alas, this kind of rule is the norm in large corporations. We are permitted to sync with a local Palm or MobileMe device. I could sync my iPhone to work if I trusted Apple's Exchange/Outlook sync software (I don't trust it), but then of course I wouldn't be able to sync to my home iTunes library. This is a big iPhone limitation for me; my Palm had the same problem.

2. In my testing of Google's calendar sync it's always failed miserably. In the last test I found it failed to sync recurring appointments. I just don't trust Google to get this working, it's clear their heart isn't in this kind of work. I won't be doing further testing since I no longer use Outlook at home (switched to iCal, etc).

I'm not optimistic that we'll see a fix to this problem from Apple. There just aren't enough people who are demanding a solution, and corporations obviously aren't incented to help non-C suite employees deal with work/home calendar hassles.

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John Faughnan
jfaughnan@spamcop.net
www.faughnan.com

iTunes lets you decide which tab you want to sync with which computer, it's not all or nothing. i sync (wirelessly) using ActiveSync (mostly works fine, some co-workers are having trouble with attachments in email), MobileMe (works fine, no issues), and a few other email-only accounts. i sync my media with my Mac at home. i like to check the "manually manage music and videos" box on the summary tab in iTunes, but that's a personal preference.

i really like having my work and home contacts and calendars both on the device, but separate. with other devices, i had to put all of my personal contacts in my work address book.