I see you have studied the designer and property editing interfaces.
I am not sure if they ever have been used the way you want to use them, but it should be possible.
Usually there is a dedicated component editor for collections.
For example see RegisterComponentEditor(TStatusBar, TStatusBarComponentEditor); (unit StatusBarPropEdit).
You can follow the code and try to make the same effect without a component editor. I don't know right away how to do it. Component and property editors are a complex issue with messages going back and forth.
To debug your code you must install your component and debug the whole IDE. It is not a problem, lazarus.lpi project can be used for it.