I’ll take a wild guess to say it has something to do with the non-requirement for “hard-refresh” @emre mentioned, which came about in v4.1.75 via this discussion regarding Automatic Customer Discounts:
EDIT: I removed the Refresh Ticket Action from the Rule, and the Caption on the Automation Command Button properly toggles between To Go and Dine In, on the second try, and each successive click, unless you add another Order Item, then you need to click it twice again for the Caption to change.
Unfortunately, the Ticket does not properly show the current value for the Ticket Tag.
However, the Print does show the proper Tag Value.