ORD Annotating XS Crossing Feature Points

I am using 2020 U3 trying to figure out the best way to handle feature crossing points (ie. right of way, fence, wetlands, etc.) in a Cross Section Annotation group. I am well aware of the right of way example Cross Section Point Annotation - Troubleshooting the Location Annotation Filter - YouTube for a single feature, but I have many potential features to annotate. It is a big ask of anyone to need to hard code all possibilities of labeling every unique type of crossing feature in and create a giant annotation group so hopefully there are solutions in place.

First, is there a wildcard function to reduce feature definitions down to prefix, suffix or contains versus adding a unique expression for every single crossing feature?

Secondly, I had the thought of using ItemTypes and named expressions to assign XS label shorthands to certain feature definitions so I could use one text favorite for a multitude of different crossing features. Oftentimes, the feature definition name is too long to show in XS and individual feature names are incremented numerically. I set something up to annotate an item type for point features, but it did not assign to the point the way it should have. I know the text favorite and item type work because in the video below because all I had to do was one-click to reassign the text field. Almost there, but close only counts in horseshoes:

Hopefully a workaround exists now, but these two small inclusions are the difference between having 4 annotation definitions versus 20,50,100+ for cross sections. It would be something a standards coordinator could easily include rather than put the burden on designers to figure out Annotation Groups every time a unique feature comes up. Thank you.