1. people trying to learn a new skill X
2. rationalists trying to understand the meta-process of learning

2 first - I meant - learning how to learn. or trying to get better at techniques of learning.

1a. sailing: I just ran through the first few points in my head (took about 5-10 minutes); and yes it seems to work for sailing.

1b. social interactions with strangers: yes it works. It occurs to me that there is no indication of how long each step should take. I am going to add that in as a guide.