Currently it appears that WORKMODE is based on hard coding in Configuration.
If I hard code WORKMODE to DGN, and I open a DWG then the DGN capabilities are assigned.
If I hard code for DWG and I open a V& DGN to migrate it to V8 then only the DWG capabilities are assigned.
The preprocessor needs an additional option to detect the file type I opened in Windows or PW and evaluate it accordingly [maybe via Windows MIME] and then proceed with reading configuration scripts.
And, if need be, in Config we can hard code additional WORKMODE capabilities, or override file type specific capabilities with my own..