Consider the bottom
I think the ease of single-handing your anchor depends a lot on the bottom type and contour. I would seriously think twice about trying to anchor alone in a rocky bottom, especially with a rapid depth change. On the other hand, with a sand or mud/clay bottom that gently slopes, I find I can easily anchor by myself. I have a C400 and use a 40 lb CQR with an electric windlass. As the sailor from Anacortes said, get everything ready beforehand--know your depth, figure out your scope, and have the anchor line flaked or laid out nicely on deck. Just as the boat stalls, go up and drop the anchor and about half the rode you actually want to use. This way if everything goes wrong, there's less rode to get tangled and get back on deck. I cleat off at this point but then hold the rode in hand--you can really feel if the anchor is digging in or dragging even before you can tell visually. Once it's digging in, go ahead and let out the desired rode and then slowly back down under power as usual.However, as also pointed out, deploying from the stern can be helpful if the wind or traffic is such that you don't have time to get up to the bow when the boat stalls. I just feel a bit uncomfortable having a line in the water not very far from my prop.Maybe I've been lucky but I've not had a problem retrieving the anchor. I pull the rode in by hand until I get the boat moving, then take up the rest with the winch. However, I'm careful to winch only slack rode, not rode under tension. If the boat stops moving and the rode goes tight, I start again by hand. If you're careful not to bring in the rode too quickly, you'll have a little forward momentum to break out the anchor but not so much as to give you a jolt if the anchor is stuck. If stuck, pull on the trip line once the boat is downwind (or downcurrent) again from the anchor.As in everything else when alone, plan ahead and take it slowly and it'll work out.