The change from OE to O is pretty easy and doesn't require much knowledge and work. But if you ever want to take the step back to OE, don't ever think about using O at all.
I use Outlook at work and TheBat! as a worthy alternative at home. In my opinion, you should better keep using the free Express version since it's as safe as the commercial one and the most basic features are available as well. What makes Outlook a great eMail client - despite all of Microsoft's security leaks - is the symbiosis of several features like said dayplanner/calendar with an eMail client.
... but can (need?) you use all that as a stay-at-home mom?
