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Rollout plan for Windows 7 and Office 2010

Our company is trying to get aligned on what we think the migration will look like   Here some items that are of question:
-Ofice 2007 or Office 2010-What is the justification for moving to 2010?
-Should we deploy only new PCs to Windows 7 or all?
-What is appropriate timing of this project?

Any suggestions?
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Tribus makes some very good points. I would like to add that having an accurate software and hardware inventory is essential before starting the upgrades. Make sure all of your software will run on Windows 7 with minimal tweeking and obtain upgrades for anything that is not current. test, test, test all of your software and any hardware you are considering. The combination of Windows 7 and Office 2010 will demand more memory than you needed with XP and Office 2003 or older. Windows 7 is much more efficiant that Vista. Also Windows 7 Ultimate or Enterprise will give you additional corporate controls such as encryption and should be considered when planning your upgrade. In our environment we spent 6 months deploying 200 Windows 7 PCs. At the same time we migrated from Novell to Microsoft file system, email, and directory services. In our environment we had around 30 different applications to consider and did most of our testing as we deployed. Time spent up front testing software would have saved us ten fold during the migration process.