My first dressage instructor was taught by an old cavalry officer. She had a very classical background. She, too, had me close my eyes while riding (a difficult enough exercise on its own) and tell her when the hind leg came forward under the horse. Like you, I was wrong every time.
It’s a great exercise, but you’re right - it just leads to more overthinking. 
If you are swinging your hips to follow a big walk striding horse, your lower body moving with the horse and your upper body still, then your legs roll with the barrel. When your leg swings in, the hind on that side is moving forward, and it’s the natural time to add a leg aid.
If your horse does not stride and swing, or if you are tight, can’t seperate lower and upper body, or if you are pumping forward and back with your body rather than letting your hips and legs swing, it’s about impossible to feel the stride.
I’m always amazed when new riders can’t follow the motion of the horses head with their hands but again it’s about being loose in the shoulders and having your hips, torso, and arms all operating separately. I can’t figure out how to get a newbie at that stage to have following hands. It might just need time.
What I’ve learned from my current “energy efficient” horse is that all this is great, but without sufficient impulsion, there isn’t anything to gather up in the outside rein. You can’t get that “strung bow” feeling without the forward from behind.
I wonder if this is what your trainer is getting at?
@Scribbler I find that complete beginners, the ones who have never sat on a horse before, often have really good, natural seats. They can follow the feel of the movement beautifully. As adults learn more, they think more and more and try harder and harder. It takes time in the saddle to then build up the confidence to do less and less and achieve “feel” once again. Children, IME, retain the ability to “react” rather than to “think” for longer, which is why I believe teaching children to ride requires a different set of tools compared to teaching adults.
I grade people’s riding competence on a spectrum from “doing nothing” to “thinking about oneself on the horse” to “thinking about the horse underneath oneself” to “just doing it”. When I trot, I don’t think about how I post, instead I use my posting to establish cadence, rhythm etc.
Picasso said he had to relearn the ability to draw like a child.
i’m all about feel…and a few times during my lesson i will close my eyes, particularly during my mare’s trot. Which is naturally quite a fast tempo and large stride. My inclination is to slow her, but she will fall out of rhythm. So i close my eyes to let go of this inclination to slow her down and just …ride. Go with her. Because THIS is her tempo. This is how she goes. Once i am able to let-loose of this fear inside of me both of us can relax and have a good ride. She is responsive to directional control perfectly, as well as having a good stop…she understands a half halt and brings herself round anytime i have to remind her. So there is nothing to fear, but yet i do. I’m old and think my bones are brittle- plus I have broken my back. And there is no need NOT to trust my mare. All i really need to do is feel her and go with her.
about that outside rein… Well for me, it depends on which direction we go! I’m learning to ride her off the wall when we go with our left on the wall because damn me, my left knee is a prosthetic and i just don’t have the nimbleness i need for that left shoulder.
So she pops out her left shoulder and leans/evades… and it takes a good deal of …oh, argument i suppose… to get her straight. My coach says to tilt her nose in a smidge, then she leans even more and i don’t have the strength/stamina there in my knee and worry about her crashing my left leg into the wall (it’s never happened btw). i have muscle enough but don’t have the torque strength in my knee to keep my leg on her correctly/enough. It is our bug-a-boo…tried my toe upon her shoulder and that didn’t work. So i’ve had to learn to ride with my whip in my left hand and tap tap tap her offending shoulder. This has helped. Hopefully i can get her adjusted so we can drop that crop aid one day.
This can be true, especially of children and athletic people but really it depends on innate balance and fear level. Lots of beginners also hunch into fetal position and squeal. And the chair seat comes very naturally especially bareback
I wouldnt think of it as outside rein, but rather outside aids. Just focusing on the rein will make you handsy - you have outside seat and a groin muscle, a leg, and a shoulder that you can use to steer the horse and half halt with.
Be careful riding your inside leg too much as a rerider until you have your balance back bc you will squeeze and accidentally push the horse too far out - thats an aid that needs to be caught by our outside seat and leg and its going to cluster if youre kicking with your inside leg and pulling with the outsude rein.
Also, doing turn on the forehand and haunches will help you refine your aids and the combinations.
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