currently (as of LayOut v25 on Mac) layered SketchUp models of the same SketchUp file will snap to tools (like Dimension) only if they are on the topmost level. If you try to draw a dimension from one model to another only the topmost model will snap to the tool. This is not intuitive.
It would be an interesting feature but when I stack or have multiple models I have multiple layers for each model… turn off one, detail the other, etc.
I would find this helpful as well. I stack different views for the same model. I always put them on their own layer, but it would be nice if I didn’t have to. Maybe if there are multiple views stacked and you are dimensioning, a pop-up could appear that lets you select which model view to reference?