I think most manuals assume that the person checking the oil is not necessarily the one who changed it.
At OC time, I put in the specified amount of oil, run it to check for leaks, and then check the level after cleaning up and putting the tools away. I also always change the oil in the same place, where the vehicles are normally parked.
That gives me a baseline, and then I always check cold in the same spot. Repeatability is the key. Like eljefino said, it's easier to see the oil when it's cold. Also, on the two Toyota 1.8 engines I've had in the past decade, the level is almost impossible to read if the engine has been running. Letting it sit overnight is the best way to get a clear reading.
Of course, one should always follow the manual for unusual procedures like drtyler posted. I've also heard anecdotes about people checking oil in really cold temps, adding a quart or more because it reads low, and then being overfilled at operating temp.