This was a brilliant post. Thank you for sharing this. It abundantly clear that you are not only a thoughtful and knowledgeable sailor but a wise one and a considerate one. I honor and respect your approach.
My physical challenges came on rather suddenly... almost like an accident. It hardly matters... but although I was not operating with the same physical strength an senses... I was operating a boat I have owned for 35 years and sailed in all over the place in every imaginable condition. Having the capabilities allowed me to do this... mostly single handed and short handed. I learned my boat very well.
I made a conscious decision to use mechanical assists such as AP and windlass. Shiva came to me new with a plaited nylon rode and a CQR. I anchored for several years manually. I was middle aged and strong. But it was hard work. Shiva is 16,000 without all the junk I have added... and she has high freeboard which makes are restless at anchor. I use a steadying sail to calm her down. Because of the windage hauling the anchor can be a strain. It's not the weight of the tackle but the force of the wind on the hull. Unless the boat is making way... I am pulling the boat to the anchor into the breeze.
My decision was informed by the fact that in most cases I am anchored relatively near other boats and at time it too close and beyond my control. I felt I needed a fast way to retrieve, escape or reset the anchor. And this has happened over the years.
My first ground tackle upgrade was to add a manual windlass. It was OK... but a but slow. If I can't get some way on toward the hook it takes a long time to get the anchor up. I was also concerned about chafe on the rode related to the metal bits at the bow below the deck... a problem in wide yawing.
When I decided to cruise the Caribe I fitted an vertical electric windless and went to all chain. The weight of the chain (catenary) will help making way to the hook. But I still need to be in a fairly narrow anchor to wind the chain in. When the angle is OK I press the button and take out the catenary boat moves with decent speed toward the hook until the wind pushed her bow off. I wait until she aligns again and press the up button making more way to the hook.
I fitted some brushed between the cheeks of the bow roller fitting. It knocks off most of the mud. If I use a hose only clean chain enters the anchor locker. LIS is muddy.
When I get close to the anchor the chain is at a steep angle and comes up very quickly. The boats momentum will usually make the boat pass over the hook and break it out. I can see the chain then begin to come up very fast with no resistance. The wind will push the bow off. If I am close to other boats I do the break out from a cockpit switch. Motor is on and transmission in neutral. I set the controls up so I can steer with the AP dial, operate the engine and raise the windlass from a good perch in the cockpit so I can observe the anchor and the close boats. AP is engaged and course set to the anchor location... so it will steer back a bit in the puffs.
I've got this down pretty well and am comfortable with setting and raising the anchor. It's not a chore. I am not tired as I was without a windlass or even with a manual one. Now with knee and back and balance problems anchoring manually is a non starter. I don't expect my body to get stronger but my anchoring technique is hardly impacted. It's second nature to me, And the electric makes it pretty quick in most cases and to me that's a good thing even a safe thing when among other boats.
Picking up a mooring is actually more difficult for me than anchoring... if there is any wind because I need to get the bow close the the mooring, go forward and pull it up and secure the loop without over running it or being blown off. When I have someone at the bow I can get the bow where it needs to be from the cockpit. Alone can be a problem. But it's not a problem to figure out where to drop the hook... let the boat come slowly to the spot and release the anchor even from the cockpit. When the wind catches the bow one side or the other I can see the stern respond as the anchor sets. Chain is marked and I not the depth and lay out the scope I need. If the boat is yawing back and forth the hook is likely set. If not the boat turns a beam to the wind and is pushed dragging not setting the anchor.
I don't how other boats behave when anchoring. I know how mine does. I know when the anchor is set, when it breaks out and so on.
I have have to replace the electric windlass one time in 30 years. I have had no failures until the gears started sounding funky. So I replaced it in 2010 after 20 years of reliable service.
As I am not going back to a hank on head genny... I am not returning to manual anchoring. I don't think my practice makes me lazy... it makes me smart. But sure... mechanical and electrical things will fail at some point.