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New PC w/Windows 7with 2 user accounts and backed up data from XP-easiest way to transfer over

I will try to keep this as short as I can but I really need help with data transfer. I have been building and selling a lot of Windows 7 custom built PC's. My customers have XP PC's and mostly have multiple users and multiple Outlook Express email accounts. I have a portable hard drive and also I am using the first version of click free back up. I just ordered the newer version and maybe that will help me with a lot of my problems. Here are my problems and Experts, I would like you to be like you where in my position for these answers. I am getting users data and emails in other users accounts when using click free back up. I was thinking using click free would be faster than the old way of a portable hard drive. Is there something else out there that works better that will back up accounts and restore them into the correct accounts?
1. How to back up data for each user account and restore it to that users account on the new Win 7 PC?
2. With new PC I am using Windows Mail Live. Old PC's Mostly using Outlook Express. How would you back up there emails, folders and contacts and import/export them to each users email account?
I have been having to spend way to much time after I have the PC built on the data transfer portion. Please show me what you do or would do in my position?
Thanks
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@moon_blue69 this is for a large network or company with up to 50 PC's migrating (upgrading) to Windows y. That is not what my question is. I am not Upgrading the PC. I am building a New PC with Windows 7 installed on it. The client has an old PC running XP. This is important that the people answering my question understand this. Now, after I have the New PC with windows 7 and I have access to the Old PC running XP. I can either backup the data to an external hard drive or use a backup drive that has a built in program that makes it easier for me to back up the Old XP PC and transfer date from all User Accounts that are on the Old XP PC to the New Windows 7 PC. Being mindful that all the user preferences(favorites, Links, Outlook Express email folder, email, and contacts over to Windows Live Mail) etc.
I am having to pend to much time transferring the data from back up into each user account and wondering what would be the fastest and best way of doing the data transfer that I mentioned. I hope this clears things up.
Thanks,
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