I switched from PCs to Macs about three years ago and used first Entourage then Outlook for Mac 2011, so I have had extensive experience with both in an Exchange Server environment and with extensive IT support from my company. In my experience Outlook has been a nightmare, and the problems I've had are too long to list here. They include ridiculously slow performance, frequent crashes, and corrupted data base files that need to be rebuilt frequently. I'm a heavy user with extensive email and calendar files. Outlook just can't handle it all. As we operate with Exchange Server, all of my Outlook files were backed up on the server. This is a good thing as owing to several serious Outlook crashes I would have lost nearly all of my files.
Two days ago I switched over to Apples's Mail, iCal, and address book, all working off Exchange Server 2010. Suffice it to say Apple's software works with Exchange Server far better than Microsoft's (go figure). I keep both Mail and iCal open on my desktop all day. They load and operate much faster, are easier to use and synch, and work seamlessly with all of the applications that I normally use with my calendar and email.
This morning I totally removed Outlook and all of its related files. Haven't missed it a bit.
I feel like a complete idiot for having suffered through all the problems with Entourage and Outlook for so long. If I had started using the Apple software from the start I would have saved myself endless days of wasted time, and worse yet, untold hours of anxiety and rage at the problems Microsoft has created with these insufficiently and poorly developed products.
My advice: don't hesitate for a minute to make the switch. Drop Outloook now and set up Mail, iCal, and Address Book. BTW, everyone else in my company uses PCs and they have issues with Outlook as well, although not nearly as serious as mine were.