[ORD 2020 R1] Using an Annotation Group on a Linear Feature Definitions with Inconsistent Outcome

In trying to setup some ideas for our ROW people, I created some Linear Feature Definitions for property takes. I also created their Feature Symbology and an Annotation Group.

The ROW people may use a lot of different approaches to define the takes. So for this to work, it should not matter how the graphics get created, anly that I show them how to assign the Feature and then to annotate it.

And therein lies the rub! I seem to have a complete hit or miss when it comes to getting annotation to display. I set the active feature and the use active feature lock. If we draw using line between points, they get the feature and will annotate. In many cases, someone will supply them with a complex shape and they will need to "civil"-ize that shape to be a Take and have it symbolize as such and also annotate.

I cannot for the life of me determine why some of the figures annotate and others do not. I have some with Rules and some without rules. Some we imported into the geometry builder and others we simply assigned a Feature Definitions. And dome annotate and some do not.

Is there some hidden toggle I am missing? At least one of these was refusing to annotate and something I did made it suddenly start - but I have no idea what it was.