I ran into an issue like this, could not load an updated SG iPad project onto a Pro2 with a CF card installed.
It is a Toolbox issue and TB does not seem to want to fix it as the hardware is too old to support.
I started downloading older versions and found one that worked:
I was still able to load to the CF on the Pro2 with Toolbox v 3.05.233.
I jumped to Toolbox v 3.0920.0042.0 (what a version number!) and it no longer works - Removeable Media option is grayed out.
