Per what I remember reading or hearing in interviews/lectures at seminars form Guro Inosanto, I think a big part of it was coming out of WW2 many of the escrimadors were tried of war/violence and went on to other jobs such as farm workers here in the states and such. To the point of not really even teaching their own off spring their arts. Plus I also remember reading other accounts of how brutal the training was with getting wacked all over with the sticks, feed a high forehand strike and get hit, then learn to block it and then add a second strike and get hit again and so on. This is not a way to promote an fighting art, you can make a good fighter, but not promote and grow an school.
Also from talks with Remy, I understood it to be that at any given time someone could ask for a lesson, or to check their stick (which would be a challenge to a fight), and therefore many people would lay low and not advertize their skills. So once again this tends to let the art die away.
The story I heard from Remy was that he was a land baron's fighter (head of security) and he gave Remy a letter which opened another opportunity to teach a person up the social ladder and this upward movement in time opened the door for Remy to talk with the head of the school systems (or a school system) ultimately teaching for the Dept.of Education of the Philppines. Remy felt it was his destiny to promote Arnis and I believe considering his background of fighting he would devise a way to promote the art and make a successful living at it.
Remy got his skill from fighting with the Balintawak gym and also from going around and fighting other masters of different styles and/or areas. I think this experience also helped him in his formulating a style of arnis that was more generalized and changed the focus to one of self defense and not just stick fighting.
Also I think it changed his outlook (on life) and his goals to promote the art and make a living doing it. I believe once Remy saw that he make a living teaching he changed his approach radically, with hitting the stick just one of the changes he made.
WWII - Many of the fighters died, and those that did not, knew about some serious applications.
Yes challenges and or checking people out happened all the time. Which is why I ask, do you want me to be a compliant partner or am I allowed to move. I ask this first, to understand the intent. If they want to check me out I want to react the way I would and that way we can see what is or would happen. If they want a complient partner I am willing to work with them and to not "play" with them so no one is embarrased. I have had this happened where they expected less from me and were surprised. I think it is still a good idea, personally.
Remy did get a lot of good training from those withing Balintawak school. He also trained with and against others.
Yes Remy did connect up with a rich and powerful person who had support ( guys with guns ) so he could fight others and not have to worry about the other side and thier guns. He also was training the "Land Baron's" (your term not mine) son. This is where he would tell stories about having to be good at disarms so as not to leave bruises on the son's body.
Quick time line: Remy Born 1936 leaves home at 14 and goes to Cebu for a few years. Leaves from there and trains and fights with others. 1957 (* The inside cover of "The Practical Art of Escrima" states: *) he was teaching at a college in Bacalod City. Remy was 21 in Bacalod, where he met his future wife and also opened his school.
From the afterwads of "Modern Arnis Philippine Martial Art "Stick Fighting" ", The Man Behind Modern Arnis:
"Remy was not only successful in that respect. HIs business in the city also went well and he was also teaching pysical education (with emphasis on Arnis ) in De la Salle College, then in the University of Negros Occidental-Recoletos, being a holder of a bachelor's degree in education major in physical education. Remy was then a very successful man, a sucess capped by the encouraging outcome of his crusade to revive the lost glory of Arnis.
Then in 1968 Remy was confronted with a decision that was to become a turning point in his life. In one of his summer sessions at the Rizal Memorial Sports Arena in Manilia, the sports Mecca of the Philippines, Col. Aresenio de Borja, secretary-treasury of the Philippine Amatuer Atheletic Federal and Director of the National College of Physical Education, Mr. Philip Moncerrat, former President of PAAF, and Professor Jose Gregorio, took notice of Remy. Upon learning of Remy's crusade, they asked him to further his crusade in Manila, the seat of national influence in any field of activity. In Manilia, the interest of the whole country would be drawn, Remy was told.
...
In 1969, Remy brought his family to Manila. He then established a gymnasium in the heart of Manila's commercial district and founded the National Amateur Karate Organization (NAKO). ... "
Your comment has it all in direct connection, and they are to a point as it was Remy's Life, but they were separate. Remy did his travels and fights then opened his school and taught in Bacalod City and then a decade later he was in Manila and was approached for further advancement and recognition of what he was teachinig.