The Google account fiasco
Explaining this is going to make my head hurt. Everything about Google accounts makes my head hurt. Let me preface this by saying I'm probably going to get some of the details wrong. Google accounts are so convoluted that the details are quite confusing.
If you're thinking about going here, you'll need to do your own research, not just rely on what I'm telling you.
Here's the key gotcha: if you move to Google Apps, you can't take your individual Google account into Apps.
Explaining this is going to make my head hurt. Everything about Google accounts makes my head hurt
That means that whatever Gmail email account you may already have, the one tied to your calendar, chat, incoming Gmail, your YouTube favorites, and on and on and on would not be tied to whatever account you get for Google Apps.
It's possible to do some finagling.
For example, you could share your existing Google calendar with your new account and give it read/write access. You could set up a forwarding filter from the old Gmail account to the new one. You could grant access to your Adwords and Adsense settings to the new account.
But other things aren't so straightforward. Have a ton of contacts in Google Chat? You'd have to go and re-invite each one to your new account. You couldn't use your existing Gmail account name, so if you happen to like your existing Gmail account name or if it's something people are long familiar with, say goodbye.
And if your existing Google account is a member of a Google Group or has sharing privileges on Google Docs documents, all of those would have to be changed to your new Google account. Add to that phone numbers attached to Google Voice, and you have a real mess on your hands.
Yes, sure, you could still use your old account, but if that's the case, and you're trying to go for an integrated, holistic whole, having to constantly switch between a new Google Apps account and a legacy individual Google account shoots the desire for a well-oiled, cohesive messaging infrastructure right out of the water.
Throughout the whole Google Apps environment, there are little gotchas about how you transition your account, and what you can and can't do when moving to an Apps account from an individual account.
Personally, I think this is ridiculous.
Most people will likely have started with individual Google accounts and gotten to like Google services, and then decide they want to move to Apps. To force people to either lose all that infrastructure, or have to do a whole pile of hoop-jumping to make it work seems wildly counter-productive.
How I made my choice
In my case, I realized it would be far simpler to move my Outlook from one Exchange hosting provider to another.
If I instead moved to Google Apps, all my long-standing Google Chat connections would have to be re-invited. I have a ton of these and I didn't relish having to explain this whole process in gory detail to the half of them that would demand some sort of backstory explanation. All of the projects and groups I'm involved in with for work would have to be changed, which would mean I'd have to assign twenty or more administrivia to-do items to some already extremely busy people.
Plus, there was the chance everything could go wrong. I had a situation a few years ago where I had a Google account, gave it a backup email address, and it decided to make some severe changes to the original Google account because it already had the backup email account listed with some other service. That situation was never fixed, because the Googlers I eventually managed to talk to said there was nothing that could be done. It was just what happened.
Add to that the fact that neither my wife and I particularly like using the Gmail interface (and given I spend so much time in my mail environment, that's important), and that there was really no cost advantage when factoring my specific need to purchase Microsoft's Office anyway, and the decision was becoming clear.
What really clinched the deal for Microsoft and against Google was the homework problem. I didn't want to have to be a squeaky wheel to my busy CBS Interactive and UC Berkeley colleagues. I didn't want to make them all change my chat names, change my account access to all our shared documents, and make them re-invite me to all the groups I rely on to do my daily work.
The bizarre moral of this story is I would actually have less service interruption and more service continuity for my existing mission-critical Google services if I switched to Microsoft Office 365 than if I switched to Google Apps.
And that's why I switched to Office 365. So far, two weeks in, it's all running quite smoothly, both my Google accounts and my email on Office 365.
I have one more story coming in this series: how I moved a half million email messages between services. That's coming next week.