[Scott]

The crush washer goes in between the drain bolt and the oil pan. It isn't always necessary to replace it at every oil change, but considering they cost about 25 cents each, there's no good reason not to.

As for siphoning oil, it's a very bad idea. Namely because you will never get nearly as much oil out. And the oil you do get out first will be the more viscous "good" oil. Over time, sludge will build up in the engine and performance will suffer. The way I see it, unless you've got very long and thin arms, it's much easier to change the oil filter from underneath the car. So you might as well put it up on jackstands and drain the old oil from the pan.