How quickly do you upgrade to new versions of software/operating systems?
At work we were recently upgrade from Office 2003 to Office 2010. We were prevented from going to 2007 due to tool incompatability issues. We're still running Windows XP. Almost everyone is resistant to upgrading to new versions of software or operating systems due to having to relearn how to do things, modify tools and scripts that we use and just the general hassle of it.
At home, I have a similar resistance to upgrading, especially upgrades with major changes. Many new features just don't seem worth the hassle to me. So I usually only upgrade when forced to do so.
How long does it take you to upgrade to new software versions or operating systems? Are you an early adopter eager for new upgrades or a curmugeon avoiding change at all costs?