@YawningDodo I found myself nodding along with so much of your post. I also did the CP (20 years ago - eek!) and for me my solo trip felt a lot like the experiences I had as a CP in the parks when I would go just because I could and sort of let the magic find me.
Everytime I go to WDW now with others I am the planner which can bring enormous pressure to maximize the experience for everyone and make sure that everyone has a great time and gets the most out of their very expensive park passes. I know that I will basically always have a great time no matter what because I love it so much but I know that isn’t necessarily the case for everyone. When traveling with others I always work really hard to cut down on transportation time whether that means not crisscrossing the parks a bunch of times to get back and forth to attractions or planning days so that we don’t spend a ton of time on buses and boats and monorails. For me the WDW transportation is part of the experience so on my own I never thought about the most efficient ways to get places, I just went. So I took the Skyliner just because. I took the boats a bunch. I rode a loop on the monorail. I visited resorts without worrying that the travel time would be too much. It was not at all an efficient use of time but I still enjoyed it immensely.
Everytime I go to WDW now with others I am the planner which can bring enormous pressure to maximize the experience for everyone and make sure that everyone has a great time and gets the most out of their very expensive park passes. I know that I will basically always have a great time no matter what because I love it so much but I know that isn’t necessarily the case for everyone. When traveling with others I always work really hard to cut down on transportation time whether that means not crisscrossing the parks a bunch of times to get back and forth to attractions or planning days so that we don’t spend a ton of time on buses and boats and monorails. For me the WDW transportation is part of the experience so on my own I never thought about the most efficient ways to get places, I just went. So I took the Skyliner just because. I took the boats a bunch. I rode a loop on the monorail. I visited resorts without worrying that the travel time would be too much. It was not at all an efficient use of time but I still enjoyed it immensely.