Staying With The Times
I never really notice how important it is to stay current with software, upgrades, and patches... until I use a computer that is behind the times. I have a large amount of forgiveness for poor computer that have never seen the internet for themselves. While it is a shame, it is forgivable.
For the 99.9% of computers that do get on the internet, it is just horrid to be three and four versions behind on FREE software, upgrades, and worst of all, security patches. If you wait ten years to check for upgrades... yes, the downloads can take a long time; however, you can save yourself a lot of headaches by checking in with your most used pieces of software. The most common thing that you use on your computer is your OS (operating system)... and is the most important thing to keep current. Microsoft Windows, Mac OS, and Redhat Linux are all really good about updating. I would suggest checking in once a month at a minimum.
Adobe is good about updates and upgrades... as well as the latest PDF viewer is nice to have. Apple's free Quicktime player is something that should be up-to-date. Too much of the web is being taken over by Flash... forcing this free download to be much needed (I am pro-SVG). Microsoft users can find pretty current updates here.