I often find upgrading quite a hassle. Some programs I use come up with updates every 2 days! That is insane. I just want software that works. Who really cares about a little upgrade that adds one tiny feature or fixes a non-problematic bug. If you want stability, go with Linux or BSD. Some might say that the applications are not the best but that is wrong. It may take a little effort, but you can get just as good programs for Linux as for Windows. I often perfer the Linux counter parts of Windows applications. Besides, Windows is so easy. I want a challenge. Ok, off topic now.
Anywayz, I find updating software for major upgrades only is quite sufficiant and I have had no problems with compatibility or stability.