Office 2003 to Office 2007. Windows XP Pro to Windows Vistax-of-6. It's all looming on the horizon, and even though that horizon moved to early 2007 as of this week, it's still going to spawn headaches if you don't make adequate preparations. To avoid ruining your Fall, you're best off planning your user-migration process now rather than in, say, November.
Just put a plan in place. Even the skeleton of a plan is better than nothing at all. Someone's going to pin you down during some meeting between now and then asking questions about estimated manpower, migration dollars, and so forth. Better to be able to pull something smart-looking off the tablet in the boardroom rather than just staring off into space and calculating off the cuff.
First off, check Microsoft. For administrators using SMS (Systems Management Server) 2003, Microsoft's done some real work on automating the user-migration process. WIM (Windows Imaging) allowed Microsoft to add tools to SMS such as the OS Deployment Feature Pack, which combines a small-footprint OS, called Windows PE (Preinstallation Environment), with SMS to download predefined XP OS images. All that with a "zero-touch" moniker, which basically means "automated."
Microsoft has also added the USMT (User State Migration Tool), which tacks on top of the SMS OS tools, allowing admins to specify which user settings are to be moved over to the new deployment. And that's far more than just MyDocs and your IE Favorites; it includes favorite fonts, display settings, Outlook Express or Microsoft Office, and more. Theoretically, you should be able to swap XP for Vista and upload every Microsoft application to the new OS using USMT.
Trouble is, few folks use only Microsoft apps, and that's the rub when using USMT. Building migration scripts for custom and commercially purchased third-party software isn't rocket science with USMT, but it is tedious and will take time. If SMS is the broad tool you're looking at to deploy Vista, then familiarizing yourself with USMT now would be a good idea.
Additionally, maybe it's just me, but I never like making application migration part of the user-specific settings process. I like defining an OS and application portfolio for every class of users (usually by department), rolling that out as part of a desktop imaging process and then updating individual user settings on top of that. Microsoft has the tools in place to handle that with or without SMS if you're willing to do a little legwork.
Alternatively, look at some third-party tools. If you've got another desktop management tool in place, calling your rep now and getting particulars on his or her company's Vista vagaries means your early summer will be much less hectic. Vendors such as Altiris and LANDesk have already made Vista compatibility announcements. Altiris, in fact, is part of Vista TAP (Technology Adoption Program) beta, so you know the code is out there for those guys.
But selecting a tool is only part of the process. Planning means taking a close look at where Vista makes the most sense in a tiered rollout. My favorite approach is to look at hardware-lease end dates. If your client PCs are coming up for lease renewal anyway, rolling out new operating systems to those users is made simpler by the fact that new hardware will come Vista-ready.
Just be sure you've tested all business applications for those users under Vista before making the move. Applications then become part of a new OS image, and user-specific settings can then be relegated to either the third-party OS management tool's features or the internal Windows tools you're already using.
Don't get pushed into do-it-all-at-once fever. Rollouts are stressful, so there's a natural inclination to "just get it over with." But having several smaller rollouts is a far better recipe for success than trying to land the big fish all at once.