It isn't hard to do it properly!
In my 20 years of boating, we've seen some unbelievable examples of how NOT to drop an anchor. Just last weekend, in Block Island, we saw a 30' express cruiser, running at about 5 knots DOWNWIND, simply drop his hook.... while he kept on going... unbelievable!Our technique has been practiced over the past 20 years. My wife, at the helm, locates a suitable spot, recognizing how much room we'll need to drop back after the anchor is set. She brings the boat up into the wind, and as the boat slows to a stop, she announces the depthsounder reading. I lower the hook, using the windlass (we use an all-chain rode and a heave Danforth anchor) and let out adequate scope. We let the breeze blow us back... until the anchor rode indicates that we've begin to dig in by pulling the bow straight. I then let out additional scope. When sufficient scope is let out, my wife puts the engine into reverse, at IDLE, to help to set, as well as test, the anchor. When we're satisfied we've dug in adequately, I use a short nylon hawser with a chain hook, letting out a few additional feet of chain so that the load is borne by the nylon; this provides some additional shock absorption, while at the same time preventing the chain from noisily shifting in the roller as the wind pushes us around.To retrieve the anchor, my wife engages the engine, once again, at IDLE speed, and follows my signals to turn the boat as I retrieve the anchor with the windlass. When I can see the anchor come up, I give her a 'thumbs up' sign, so she can proceed slowly while I clean up the anchor and stow the related gear.