If you need to do an "Is One Of" in the console, I believe you are going to have to use LatestAssignment.Group.Title. The Is One Of, based on my experience, has always accepted string values in the form of a list. I haven't tested this myself, but it should work using the .Title attribute for that business object.
I agree that is does function a bit different in the web but hopefully that will change soon.
You're right. In fact I forgot to mention what started all this. Initially I'd found that to be the case and that's how I got around it. You'd have to type the full title of the group and hit enter for each one which was kind of silly, but at least it would work. After upgrading to 7.8, the team requesting this was no longer able to do that. It appears to have broken You type the name and hit enter, but nothing ever applies.
I haven't tested with 7.8.1...maybe I'll give that a shot and see if it's fixed in that. We probably won't upgrade again so soon, but it'd be nice to know if a fix is on the horizon.
You could also give LatestAssignment.Group.Title CONTAINS prompt user... that might give you a better result.