Enjoyed the story. I sail solo most of the time. Even with wifey on board she won't do a thing... and doesn't want to learn. She's company and that's fine.
We have a mooring so getting on and off is usually no problem at all. Above 20 it is a bit of a challenge.
When I do reef I will motor head to wind with the autopilot and have enough forward motion that she stays bow to wind.
I store in water so there I deal with a slip and prefer bow in for privacy. Getting out of the slip I usually take the line and walk the boat out and hop on at mid ship. She has some momentum and usually it doesn't even require any prop at all. When out of the slip I use the prop and steer.
Getting in is also simple since I use a mid ship cleat and make the line fast (and short) which completely stops the forward motion. I then take the bow line and pull the boat forward into the slip... after letting the mid ship line run around the far post/cleat on the dock which will be for the stern line. The mid ship cleated line is then made fast as a stern spring. Voila! Finally, the excess bow line is brought aft to the midship for a bow spring.
Sailing in crowded waters is hardly as enjoyable as it is stressful and worse so for single handed sailing.