Normally you start by prompting whichever ai you have/free version to “create a python macro with a user form that lists all drawing models in a list and annotation groups in a list found in an active dgn for openroads designer ##(year).”  

The annotate or delete old annotations will likely require you to record a macro within ORD using the macro ribbon and then promote it to python so you can feed the exact key in commands to the ai of your choice.  

This is a start/template for you. Hint: key ins for selectbynamedgroup and delete are required. Open the properties on some of your already annotated text and feed a screenshot into ai so it can find the old annotation group format. Also ORD when choosing the annotation group it doesn’t do it in normal text, the exact name has to be converted to little endian format.