I feel that this is all getting a bit too complicated. Flash, as routinely used by wedding photographers in bright sunlight conditions to add a bit of sparkle and reduce unnecessary high contrast, doesn't need to be off-camera, or to be modified in any way. Obviously, this all changes when the flash becomes the primary light source, at which point one or more much more powerful flashes can be used to create light, rather than to supplement the existing ambient light.
Different people have different ways of working and that's generally a good thing. There are no set protocols or procedures with most types of photography, and if there were then the result would be that everyone would produce exactly the same results as everyone else. . .
With respect, I don't feel that this is relevant. Wedding photographers are highly visible and don't hide in the shadows the way that Cartier Bresson did - and anyway, he didn't have our excellent, modern equipment. Flashbulbs, because of their very slow burning, produce a much more obvious distraction than small electronic flash units.
Weegee had no choice, he had a day job and took all of his photos (mainly of crime scenes) at night, using a 5"x4" plate camera and a big flashbulb, his lighting was terrible but he was successful mainly because he was the only one who had the contacts and who could be in the right places at the right times.
Flash, used as fill in bright sunlight conditions is always a positive thing to do, there is no downside.
The easiest and possibly the best solution for you is to always use the camera in landscape format when using flash, that way you won't need to worry about the orientation of the camera / flash combination. Obviously this will lead to some loss of image quality when you crop from landscape to portrait but this should not be significant and anyway it will become much less of an issue when you move to FF.