Everyday someone release an update for x. Weither it be an important upgrade or a fix to a typo.

I say no, because of the simple fact that programs such as Apache and PHP, don't do to well to upgrades.
Apache: Say you have your Apache 1.3 installation all happy and installed with 5 modules. Why should you upgrade to Apache 2? Because your Apache 1.3 modules won't work with Apache 2. So if you really want to upgrade to Apache 2 you have to modules that were created for Apache 2. Waste of time IMHO.

PHP: Some (not all or most) older scripts won't work right on PHP 5. So, why upgrade to PHP 5 when your PHP 4 install is happy and working properly?

Again with this poll, if you vote please say why you vote that way.