The reason I say it is a bug and not working as designed is that a command should never show you one piece of data and then blow it away without letting you know why. There is no cancel button on that dialog, it is what we call light weight, every change you make happens immediately and when...
Interesting, I tried what you said and indeed it did what you said. This seems like a bug to me and it would probably be good if you could submit an IR to GTAC if you haven't already. I am glad this worked for you :).
I am very perplexed. Here was the steps I took (basic I know, so if there is something I am missing then let me know).
1. Insert a sketch line
2. Insert->Dimension->Inferred
3. Select the sketch line and then toggle off driving dimension
4. Edit->Annotation->Text
5. Select the dimension
6...
In case you haven't contacted GTAC yet then I think there is an easy solution to your issue. The dimension commands have a "Driving" group on them with a button in it. After you select the geometry for the dimension the button will become sensitive. The initial state of the button is...