Good Points. Wing Chun came from the Red Boat Opera. Problem is that there we over 40 Opera troupes in Foshan . Troops gathered in winter and went their own ways in summer. Many members had martial skill. Wing Chun was not a religion then so 1 troop might combine more crane and another might cross with other arts based on the skills of those in that particular troupe. Then it spread but that led to the next problem .Some say their wing chun was learned from painted Face Kam for example. Question is which one there we over 40. Stories say Leung Yee Tai sang female roll others say he was a pole man. Both could be right and talking about different people. So this is a core reason there is no one format wing chun never had one strict beginning. Even the base art was not called wing chun it was a form called SLT.
Second reason is that wing chun developed as an elite martial art. Not elite as in skill but elite as in who was taught. It became the art of the business and upper middle class . It was very expensive to learn. Not like the large CLF or Hung Gar schools. For whatever reasons many wealthy business owners hired private wing chun instructors for their children. Most of these people never went on to teach and never wanted to so there was very little sharing across the different styles during the late 1800's early 20th century. Leung Jan and his students were the most widely known but Leung Jan never claimed he was the only source. The largest standerization period happened in the 1920's when Ng chun So was teaching at Yui Choi's brothers business and for the first time wing chun had its own gathering place where practioners hung out. This is when the 3 form platform became as close to a standard as there is although the composition of the 3 forms varies.
"Very expensive to learn".
This is a really important insight, because by expensive you mean cash, and in Chinese terms around the times we are talking cash was a string of copper coins, unless you were wealthy and had more precious metals or trade goods.
But earlier on, from the time Wing Chun draws its legends from, this kind of knowledge really came FREE from very select places: a monastery, a pilgrimage, a military trainer, and often a combination. Or maybe traveling artistic nomads, like you say, that sort of bridge that gap between the Ming-Qing era. By the 19th century, things were commercialized. By the 20th, national politics ruled.
But there is no cost in the early Shaolin traditions other than submitting to Buddhism. You could be as poor as dirt and still learn art forms that survive to this day.
But today 2023, this knowledge doesn't come cheap, does it. You need cash.
And I think, pet theory, this is why Wing Chun also dominates cinema today, out of all of the kung fu styles.
But it wasn't always that way. To this date, the Hung Ga Kuen still dominates historical cinema. I forget the exact number but more than 100 movies about Wong Fei Hung, but a fraction of that with Ip Man Wing Chun has made, money wise, boat loads at the box office.