Adding Project Settings in one section over multiple classes?

One technique that might work here is to use the decorator pattern: Decorator Design Pattern

What it would allow you to do is split up the functionality of adding your settings through RegisterSettings and handling their changes in PostEditChangeProperty into different categories or groupings. When your main custom setting class wants to call RegisterSettings it calls this function on each of its child decorator list, allowing them to fill the custom widget list before actually calling the RegisterSettings function.