I don't do that much hand sailing as I did years past. However, just let another sailboat on the same course, & let the games begin.
Otto, my autopilot does most of the grunt work for me. This frees me up to do slight sail sets for the heading/conditions/speed etc., chase a wench, or troll.
A good practice I use for dialing in sail trim is to set a course, turn on Otto, and tweak your points of sail. First try close hauled, close reach, beam, broad, running and watch how Otto reacts. The more balanced your boat becomes, the less you will hear Otto work. This can be fun as I let friends do this and they become more confident.
You know your getting good when you can tame a broad reach or a wing-n-wing run & stay the course for a length of time.
CR