I have been working on a python script to help reduce time spent on data requests from external engineering firms. These firms use the gamut of CAD software (Carlson, Microstation, AutoCAD, etc.). So file formatting an export can be difficult. For compatibility sake, we export in r2004.dwg. However, the annotations created in ArcGIS Pro do not appear when using the Export to CAD tool, rather a polygon footprint is populated where the Annotation should be.