So... I've given both skins a shot, I've tried to understand how GlassAMP even works and how it does it's windows, or some of them at least. I can't to the best of my abilities implement it to my VGUIBase branch of DeClassified,
here's the very base of window creation in the engine and is my vector point of trying to do what I want to do.
However, the big issue is how some windows seem to have issues being on top even when focused, the components likes to hide behind other windows/the main window, Winamp 5.666 also does this.
So, even if I were to somehow manage to pull off what I want to do, I would be plagued with windowing issues.