Read revvy's bottling sticky thread. Many many pieces of wisdom there.
If you pull the auto siphon high enough before you press down you'll only need to do it once. I always siphon an entire bucket of oxyclean to clean and then I siphon a bucket of starsan. This way I know its clean and sanitized.
One thing no one ever mentions vinyl tubing tastes like rubber at first, running lots of hot water through it multiple times will ensure that you get that taste out. Same with new auto siphon.