Leo thinks that Windows 7 is the best version of Windows ever. Microsoft has decided to move everyone to a tablet interface, with big tiles that can be tapped with a finger. Windows 8 is really designed for touch, and is a hybrid between a desktop and tablet interface, which makes it confusing. If Rick can get a Windows 7 system, then he should do that. If he stays with Windows XP, he'll be vulnerable to attacks when Microsoft stops supporting it this Spring.
Rick says he uses AVG antivirus and Spyware Doctor currently. Leo advises not installing either one of those on his new system because Microsoft offers a free program called Security Essentials. The antivirus software is only a backup to Rick's behavior, though. It's easy for viruses to bypass antivirus programs, so he just needs to take caution when opening attachments in email and when downloading things online.
Rick is backing up his computer to a MyPassport hard drive. He has a lot of business documents on it. He should make sure to have multiple copies of each of his files. Ultimately, he should have 2 copies on 2 different forms of media, and another copy that's off-site.