This applies to transfers from a Windows 7 32-bit machine to a Windows 7 64-bit machine.
Moving Outlook: I followed the instructions here, and they worked http://office.microsoft.com/en-us/outlook-help/move-outlook-information-to-another-computer-that-has-outlook-2010-installed-HA102544948.aspx. You will need to set up your accounts again, but unless you have dozens, it’s no bother. I had several and it was painless.
Caveat and more tips, see https://demtigerpaw.wordpress.com/it-worked-for-me-links-to-tech-tips-ive-known-and-loved/