Is there any reason why I shouldn't skip Windows 7 and upgrade to Windows 8 instead?
When I outfitted my office with PC's a couple of years ago, we were able to get the license downgrade from Vista to XP Pro, and that worked wonderfully. That meant we could keep all the versions of applications that our user base was familiar with, and not make changes to the server hosts either. Next year when Windows 8 comes out, we'll be about ready to replace these pc's with new ones. Is there any reason why we should be considering a migration to Windows 7 before 8, or will we be fine by jumping over 2 operating system versions. It's taken awhile, but our vertical market apps have been recoded for Windows 7 and should work just as well under Windows 8 (although we do plan to test them first).
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Your Windows XP workstations are all running the 32-bit version of Windows (almost everyone is), which means that they can only run 32-bit applications. The 64-bit version of Windows 7 is by far the most popular, and Server 2008 R2 only comes in a 64-bit version. It's highly-likely that Windows 8 will also be 64-bit only, and that will mean that when you make the jump to the new operating system, all your apps should be 64-bit capable. You may want to wait until next year when Windows 8 is out, rather than worrying about the migration now. After all, how many times was Windows Vista delayed? I would never hold my breath based on a Microsoft calendar.
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I'd recommend waiting for the first Windows 8 service pack before jumping to it. The last thing you want to do is install a new Microsoft operating system without letting them squish any bugs in it.
Historically, it's always been a good and reasonable idea to wait for that first service pack. I don't think Windows 8 will be any different in that sense. Better to be safe than sorry.