I have a similar setup to you with computers, and I’m making the move to the cloud, too.

But I decided to sell my soul to Google.

I got the Google Apps paid version of Gmail last summer and started pulling in my email accounts there as a redundancy to my PST file in Outlook.

But recently, I decided I’d had enough of installing loads of software every time I get a new computer, and also dealing with the dread that Outlook could screw up any given day.

It’s a little tough here and there to convert to Gmail from Outlook (the Tasks in Outlook have dictated my life for years), but the tools at Google, as well as third party apps like Remember the Milk have solved my problems.

Good luck with your move. I’m putting Outlook to sleep tomorrow – right after I bring my inbox to zero emails.