What's the easiest way to transfer files to new mac?

My first mac was a Macbook (purchased in August 2010) and I'm upgrading to the new 13" Macbook Pro with retina display. What is the easiest way to:
1) transfer files to the new laptop
2) delete files off my old macbook to share with a family member--possibly thinking of return to factory settings.
I have a 1TB external hard drive and I use the cloud on all of my devices (also have iPhone and iPad synched to the cloud).

Welcome to Apple Support Communities
1. The best way to transfer files from another computer is by using Migration Assistant > http://pondini.org/OSX/SetupLion.html Your new MacBook Pro will ask you to restore from another computer during its initial setup.
2. If you haven't got a lot of apps you installed, you can just create a new user and delete the old one, so you won't have to reinstall Mac OS X.
To do it, open System Preferences > Users and Groups (or Accounts), press the + button and create an admin user. Then, log in this user, go to System Preferences > Users & Groups, and remove the old account

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