The hard part about anchoring is planning for the unknowns and uncertainties, such as how another boat is anchored, how much is the wind direction/speed going to shift during the night, should I set an anchor watch.
The easy part is actually dropping the anchor, right? Well, not always. Let me illustrate by sharing an anchoring incident on one of our Adventure Learning courses in the Caribbean.
We found a nice sandy area in 25 feet of water, well away from coral heads, and there was only one other boat in the anchorage. The students/crew went through the standard anchoring procedures and in short time we were settled. When we swam over the anchor to check the set, the anchor was just lying on the bottom with a big pile of chain on top of it. We discussed the issue, and came up with a simple procedure that would prevent this from happening in the future.
After weighing anchor we made the approach back to our anchor drop point. Motoring slowly into the wind, the helmsman brought the boat to a stop about 20 feet past the anchoring point. The anchor was lowered about half way down and we began to reverse slowly. As we began to gain some sternway, the crew lowered the anchor so that the anchor hit the bottom while we were moving, and the chain was laid out in a neat line behind it. No piling up the chain on top of the anchor.
A simple little thing, but significant enough that it is now part of the standard anchoring procedures that we teach at Outbound Sailing.