For some reason, I'm hearing the subject line of this post in my head to the tune of KISS' "Cold Gin." I don't think upgrading Drupal is anywhere near as much fun as gin drinking, but it's got to be done, and it isn't going to happen by itself.
We're currently on Drupal 5. Drupal just launched version 7. If the past pattern holds, we'll actually have to upgrade to version 6 and then on to 7. January is a pretty quiet time for the site in general. And the site is pretty quiet at them moment, so I'd like to get it done before the end of the month. I'll post anticipated downtimes when I set a solid date for it. But, if you notice any weirdness, that will likely be the cause. I'll post updates to this thread explaining whatever happens and whatever outages we experience along the way.