KeePass features its own random password generator, so you don't have to come up with random passwords on your own. It includes a quick-search box where you can type just a fragment of a website's name to quickly find it on your list. The list itself is built to contain thousands of records, and you can subdivide it into folders and subfolders to keep things organized. KeePass isn't limited to just usernames and passwords, either: Each entry has several other fields, including a free-form Notes field for securely storing any sort of text.
One way the baddies circumvent password protection is with a keylogger: an application (or a physical hardware dongle connected to your computer) that sits in the background, quietly logging every single keystroke you type, and later transmitting this information to an attacker. With a keylogger installed on your system, an attacker could potentially learn every single word you type throughout the day, including all of your usernames and passwords.
KeePass protects against keylogging with its AutoType feature, which saves you the trouble of manually typing individual website passwords. KeePass pastes them into the browser window using a combination of virtual keystrokes and clipboard obfuscation, making it all the more difficult for a keylogger to figure out what the password is. AutoType is sometimes finicky, but when it works, it's very useful. KeePass also lets you enter your master database password in a prompt protected by UAC (User Account Control), blocking any software keylogger that isn't running with administrator rights on your machine.
Get KeePass, and start using it right now. You'll thank yourself next time a major website breach vents thousands of usernames and passwords into cyberspace.
For your files: TrueCrypt
Let me guess: You use Dropbox. Or maybe SkyDrive, or Google Drive, or one of the numerous other cloud file-hosting services out there. These services are invaluable for synchronizing data across different computers and mobile devices or sharing it with others. But here's an interesting bit of trivia: Did you know some Dropbox employees can access your files? Granted, that they would do anything with your data is a far-fetched scenario, but why take the risk? The free utility TrueCrypt lets you effortlessly encrypt entire folders, so your cloud-synced data remains truly yours.