We recently moved from using Exchange to Google Apps. The transition has gone really smoothly, but there have been a few hurdles - mainly surrounding synchronization of Mail and Calendar across multiple devices.
While the Google Apps are all web-based, accessing them in a browser is not always an option - particularly when on airplanes. Additionally - if you rely heavily on your calendar for reminders like I do, remembering to keep a browser open on your calendar page is just one step too many. 
So - here's my device situation:
Under Exchange, my notebook and workstation would connect to Exchange for email and calendar, and synchronization was automatic. My phone would pick up email via IMAP to Exchange, but the calendar was synched when I connected the phone to either PC via a USB cable. Overall pretty good, but the calendar synch to the phone was a little more involved than I'd like - why not synch over the air?
Anyhow, with the move to Google, I can of course access mail and calendar from all three via a web browser. This is fine for email on the PC's, but a little less than optimal for the calendar. Needing to have a calendar open to get reminders is not good for me. Call me old school, but I like Outlook - as far as email and calendar go - it works for me.
Connecting Outlook with Google Apps
Actually getting a single instance of Outlook talking to GMail via POP or IMAP is pretty easy, and well documented. If you use IMAP, then you can have multiple clients systems connected and everything is synchronized for you.
The calendar is another matter. For PC's you need to run the Google Calendar Synch, which will copy items between your local Outlook calendar and a Google Calendar. It does the sync on a scheduled basis, so there may be some lag, but since you are planning things in the future, a 10-30 minute lag should not be a big deal.
On my phone, I'm using Mobile Outlook connecting to IMAP for mail, along with GooSync keeps my mobile Calendar in line with my Google Calendar. What's sweet it that this works bi-directionally - over the air - something which was not an option with our Exchange setup.
If you are thinking about jumping to Google Apps, I'd say go for it. The transition has been smooth and everything we need is working with a lot less headaches for our IT staff.