I did two today myself. One for me one for the wife. My watch was delivered by UPS around 12:30. I had to pair it to another phone first to update to 2.2, do the update, unpair it and then repair to my phone where my other (already on 2.2) Watch is paired. Under 2 hours for all of that.
My wife's took about 30 minutes longer. Had a few issues with it. Weird as it's always her device that causes trouble even when we have otherwise identical things.