I embed the tiff, using Raster tools. So there is just the file name to contend with.
The title block needs to update just at the time of running the script.
I've worked on ~2 dozen projects with this client, and once we set the name on existing dwgs (TIFFs) they don't tend to change. However, we have to generate names in the clients database for the new DWGs. We don't have a method to delete.. so we have a our own temporary naming system. Once we get past the Constructability Review. We enter the DWG names into their database, and finalize the names of the CAD files.