1. In various stages you mention backing up and restoring data on user machines. Now might be a good time for a policy change to centralise this on a network drive. This can done in advance of the endpoint rebuild.
2. Nowhere do you mention analysing the change in network traffic caused by the upgrade. I saw one upgrade (to NT4) bring a company's national network to a standstill. Might be a good time for a full network map and a bit of bolstering. And how about a field test in a 'friendly' department.
3. Keeping in touch with customers is always a good idea! So a regular communication plan will smooth the way. It might seem strange that people will question why you are improving their system ... but some think the money is theirs and XP is fine. Any latent distrust/compaints about IT will surface: be prepared to diffuse them.
4. A training plan might help. It is also a good place to reaffirm/change IT guidelines and policies (e.g. security). Areas with IT expertise will be more receptive if the upgrade is part of a clearly defined IT strategy. Areas with low expertise might warrant an 'expert user' who has had a chance to use the new system. This will save countless help desk calls and more importantly speed the transition.
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