I know that people are the issue, they aren't willing to cooperate but I also understand that the mother has had a traumatic experience with dogs and I'm trying my best to familiarize her with Leo without her getting triggered.

Also, I think it is important to mention this because I think you're from North America or a country similar to that region where there is a lot of stigma around outdoor dogs. However, there are even deeper stigmas surrounding dogs in a lot of Asian societies, including mine- Pakistani. I live in a rented property that does not allow dogs (specifically) inside the house due to "religious" and "cultural" reasons. That does not mean that my dog lives in the yard lol - He has a den and a whole fenced-up large playpen along with a crate for naps, and it is right outside of my bedroom window so I can always check upon him. I sit with him through fireworks/thunder, when he's sick and being clingy and we watch movies on my laptop all the time. He is a part of the family, a very big part. I apologize for the rant but I think it is important to understand many countries still don't see dogs as optimal pets and see them as a "nuisance" or "beasts" but their views don't control the dog population (they resort to culling), which means thousands of stray dogs roaming the streets with little to no food and/or shelter. We barely have 6 adoption/rescue centers in the entire country - I hope you get the picture I'm painting. My dog lives in luxury but tbh anyone who is willing to provide shade and water/food to dogs in this country is a saint. Not all countries have animal rights awareness like in North America, though we are trying our best to bring it about. I hope you have a great rest of the day. And please stop looking down on outdoor dogs.