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Should I upgrade from XP Professional to Vista Business and then upgrade to Windows 7 Professional? Or, try to do this "migration" thing from XP to Windows 7?

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Definitely use the migration tool John T mentioned. With upgrades you get some "cruft" left from the previous install slowing the system down. With 2 upgrades it's almost guaranteed that you end up with an extremely slow system.

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Yeah, upgrade plus upgrade would equal a very messy install. I'm not a big fan of upgrades in the first place but I think you would be better suited by going straight to 7. Plus if you have to reload your system often like I do, my wife and 2 year old can be hard on a computer, then do you want to have to load 3 operating systems or 2? – Daddy Su Sep 10 at 1:24
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Save yourself some time and just use the User State Migration Tool from Microsoft. This video on Technet explains the process in detail.

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