It's cheaper for you to buy MS Outlook 2007 because I have also read that Outlook 2010 has issues when syncing with iTunes so who knows what Outlook 2012 will bring.
I'm using MS Outlook 2007 and iTunes 10.5 on my Toshiba PC and it works perfect. I also use it here on my Mac Air (Lion) with Parallels 6 and it works great with only 1 issue: When I click on the App Store in iTunes it crashes. I just posted a new thread asking for info on that but if you're like me and don't use app store that much anyway then it's not a big deal. I can always use the Toshiba for now until this is fixed.
Since your most important thing is syncing iTunes with Outlook in the Windows VM then go for it because it works great. Just make sure you install iTunes for Windows 64 in the VM and don't use iTunes in the Mac OS side because it won't sync to Outlook.
Last edited: Oct 15, 2011