One of the good things about Linux distributions such as Gentoo, Debian or Arch Linux is that you never have to worry about these things. Both Linux distro's will update any outdated software (not only the OS stuff but also apps) with two commands. This is why I have on many occasion said that many who say that Linux needs an software install method like Windows don't know what they are talking about (that would be like taking three steps backwards). Those who say things like that have usually only experienced RPM distributions (even though those are now also building in similar functionality with 3rd party apps).
So on Windows you need to search, download and install (and sometimes even uninstall before install). On my Linux boxes, I do "apt-get update; apt-get upgrade" or "emerge sync; emerge -Ud world" and all software is updated.
So don't say "Sigh"! Use a superior OS!
(Btw, the packaging system and the unnecessary "versions" that RPM distros use are the biggest factors for why I don't use them)