In the Utility industry, we use annotation about 95% of the time. Please consider the following improvements to placing annotation:
1) Move the "annotate selected features" command from the TOC, to a right-click on the map while using the Edit tool (pointer). It's a hassle click on the selection tab and then scroll to the layer of your selected feature every time you want to annotate.
2) Once you have chosen to annotate the feature, put the annotation text right on the cursor as a "ghost" image and allow the user to drop it where they want it on the map and then rotate it, all in one step.
These 2 would be HUGE timesavers!