I use Truecrypt containers for my personal information such as passwords or other stuff I need to secure. It is free, reliable (never had a problem in perhaps a decade of use) and it is easy to back-up containers. I use RoboForm for all web passwords (free for up to 10 passwords I think) and I bought it since I do have more than the 10. No problems in using that either. All the passwords are stored in a Truecrypt container as well. I have to remember a secure password of about 20 characters to access either Truecrypt or Roboform but since I tend to use this frequently it is not a problem. The easiest way I have found is to 'chunk' semi-random characters until they can be concatenated and subsequently remembered and this key password is NOT written down anywhere. I could use one of greater length if I wanted but I consider 20 to be adequate.
As to web security well I seem to be living dangerously were it not for the fact that I have NEVER had any malware in over a decades use. I use NIS and SpywareBlaster, run as admin with UAC off, use IE9 for most normal web-browsing and the latest Firefox for anything else - run in Private mode with cache to memory and I use Noscript. I use CCleaner after EVERY browsing session (erasing with single random set) and I do this EVERY time I access my bank or buy anything on-line before continuing browsing. I have separate e-mail accounts for bank, purchasing, and general correspondence, and never open e-mails I am not expecting. I am careful as to where I download any software but I have several free apps that appear to be reliable as well as much bought software. I don't play games, do any p2p file-sharing or any other possibly illegal downloading. I think the latter is the problem for many rather than malware from web-surfing.
I use a second HDD and USB drives to back-up all my data and I image my system partition using Macrium Reflect free edition in case I need to recover from problems. I have used Macrium many times to recover from software problems and this too is very reliable in my view. I image about once a month now and the last restore I needed to do was over a year ago.
Just to add, I wouldn't recommend running as admin with UAC off but for me personally I prefer the greater control over my system and more convenience for me that this supplies.