Speaking as a user rather than a dev, even the current package management system is better than what we have on Windows. On linux, my libraries are six months out of date because that's how long it takes the community to add them to the repositories. On windows, my libraries are anywhere from two to six years out of date because that's the version that's distributed with each program, and my programs are anywhere from six to twenty months out of date because that's how often I reinstall my OS and go looking for new installers. I'll take Linux for now. It could be better, but it also could be worse.
If there's every a security bug in a library, you're left vulnerable until the patch is issued, and then every individual maintainer patches their binaries, and you get around to installing them. With dynamic linking, you just have to patch the one lib package and you're done.
The other nice thing about packaging systems is that you can choose how fast you want things to be updated. If you're having trying to install Gentoo on a toaster oven, things will break; if you install Debian stable, you'll never have to worry about an update again.
