Maintain Compound Path Appearance While Changing Width and Height

Catie,

I for one am uncertain:

From your description you have a (compound path) rectangle with a red line that is 2" by 2" (2 inches by 2 inches) but the rectangle shape is 2' by 2' (2 feet by 2 feet = 24" by 24"), in other words 12 times the red image, which seems to be inconsistent with the image. Correspondingly, 4' by 4' (4 feet by 4 feet = 48" by 48") is 24 times the 2" by 2".

The image could be (mis)interpretated to show a compound path with a red fill and with the inner and outer boundaries coinciding the inner and outer paths forming the compound path, all on a paler and more greyish background; but the dimensions of the outer path are less than 20% greater than those of the inner path.

The image could be (mis)interpretated to show a red stroked path on top of a paler and more greyish filled path, but then there seems to be no compound path.

I have a feeling that it is neither.

Can you elaborate?

Illustrator can either measure the rectangle by the actual path or it will do so respecting the stroke width and effects.

This is what the preference setting "Use Preview bounds" does.

On top of that you can scale the stroke width proportionally with the size of the object. Preferences "Scale strokes & effects"

But: when both options are turned on, then Illustrator cannot calculate everything correctly. It will need several attenpts to come closer.