Not such a pain!
Patches outside the regular Patch Tuesday update are a pain for administrators and Redmond has done a good job in cutting down their frequency over the last three or four years. Microsoft has been battle-hardened from years of combating Windows bugs and its security practices have become an example to the rest of the industry. Some also argue that it encourages hackers to divert their attention away from Redmond and towards exploiting vulnerabilities in third-party software, most particularly Java and Adobe applications.
They may be a pain, but getting infected is a bigger one for me. I welcome them with open arms.