There are many ways to create an air gap between yhr back of the siding and the drainage plane of the wall (WRB, exterior insulation, surface of ZIP Sheathing), here are at least a few options.
Edge metal, valley flashing, dormer, chimney, and kickout flashing shed water away from the connections between roofs, walls, chimneys, and other building assemblies
Windows are big holes in walls that must be sealed against wind, water, and heat. This guide covers scope of work, how to install them, and why it matters.
Everything* you need to know about adding insulation to the outside of old homes with cold bones