To echo the other comments, excellent story. I enjoyed reading your post.
But honestly, which of us has the better deal?
The great advantage of the Western way is that any rider with few words of instruction can sit in the big comfortable saddle and ride a well schooled western horse.
This misunderstanding, I think, is the crux of your dilemma.
A well trained horse is a well trained horse. Good riding is good riding.
I know plenty of "western" trained horses that I would _never_ pair with "any rider with a few words of instruction." Even a well trained western horse can be a problem for a rider that has heavy hands - in that case many english "school" horses would be a better choice because they might be more tolerant to inexperienced hands on the bit.
If you train a horse to be an arena horse, it will be a potential problem on trail. If you have a well rounded horse, it will be more forgiving of different situations and different riders. I don't think this is an english/western thing. At the risk of over-generalizing, I would say that some english schools emphasize the "arena" work while most "western" training emphasizes a more rounded approach. These approach is more consistent with the goal of the training.
On the other side of the coin, compare a horse that knows nothing but western pleasure to a horse that does hunter pace and fox hunting. Which one would you think the better trail horse?
I think the problem also lies in the rider's goals. A young rider taking lessons to show dressage or jumping doesn't want to think "outside the ring." If that competition is popular in your area, the instructors will concentrate on doing what they need to make the student competitive. They are not training horsepeople - they are training kids in a specific sport. The approach is more linear. The higher the level one aspires to, the more focused and linear that training becomes.
While western riders may be more laid back in their approach, some are not without the same mindset. There are barrel horses and reining horses that never see the outside of a ring either.
As it is, I am even hesitant to ride DiDi in front of the perceptive eyes of her current instructor. After almost 40 years of riding I am reluctant to take my own horse along a country lane because I know she will be skittish in a close urban environment
After 40 years of riding you shouldn't give a hoot what anyone thinks of your riding. :) You should ride to please yourself, not others. (And if you aren't happy with your current skills, work to improve them).
In the same vein, after 40 years I am sure you have the skills to train your horse for a ride along a country lane. It is just a matter of getting in the saddle and working on it.
The only danger is that once your horse discovers the wide open world out there, she may realize how terribly boring ring work is. Then she will be the one asking to move to Texas. :)