Outdated software isn't that big of a deal if you're using decent security tools. And new versions often introduce problems.
Not so sure, but it's also true that some softwares have so much bugs to require continuous updates - see JAVA RE or Flash Player - and it's boring and frustrating. Luckily I don't need Java !
Agreed, unless it's the browser and especially plugins, as these are typically a prime target of drive-by exploits. Adobe plugins (especially Flash), mentioned in the post, has especially been a swiss cheese full of security holes over the years, and why it's been a popular target for so long. Thank goodness Flash is pretty much dead.
Yes, Flash has been the biggest problem, but it's pretty dead. But believe it or not, I almost never update my Windows OS and I often run old versions of browsers, and not a single problem. With anti-exploit software and ad-blocking extensions you should be good, especially since browsers have become safer.
