Make syrup: Place 1 cup water, 3/4 cup packed light brown sugar, and 1/4 teaspoon kosher salt in a large saucepan. Stir and bring to a boil over medium-high heat. Reduce the heat to maintain a simmer and cook for 5 minutes. Then add bananas and boil 'till tender and translucent.
Add tapioca and 1/4 teaspoon vanilla extract, stir and combine to prevent clumbs and cover then refrigerate till cold (2 hours)
While that's happening, cut jackfruit.
Make milk mixture: Place 2/3 cup coconut milk, 3 tablespoons evaporated milk, and 3 tablespoons sweetened condensed milk in a small bowl or liquid measuring cup and stir to combine.
Assemble the halo-halo. For each serving, layer the ingredients in a 16-ounce glass in the following order: 1/3 cup minatamis na saging, 1 scoop coconut or ube ice cream, 2 tablespoons macapuno, 2 tablespoons ube halaya, 1/4 cup jackfruit and syrup, and 1/3 cup coco de nata. Top with 1 cup shaved ice and drizzle with 3 tablespoons of the milk mixture. Add more shaved ice to fill the glass if needed.