For day-to-day purposes, I think a better question is whether Wolfram Alpha's updates are as fast as, faster than, or slower than whatever other source you might use to check such things. Consider the periodic posts of television news getting this badly wrong: one recently, illustrating current events in Ukraine, had Czechoslovakia as a single country. Information propagates weirdly; one of my occasional tasks at a previous employer (which I took on because I noticed it needed doing) was updating our address database to track such things. We had a number of contributors in what had been Czechoslovakia, so go city-by-city and change them to Czech Republic and Slovakia. Before that, I'd had fun calling the Estonian Consulate to New York in 1990 and asking how I should address letters to Tallinn (answer: yes, keep using the long Soviet post codes, at least for now).

If I was doing any sort of historical research, the problem would be the reverse: when electronic records update, the updates may not be time-stamped. When exactly did this border shift, in practice as well as on paper?

I would hope people who are traveling where the boundaries are changing know at least some of the risks, and are getting information updated in a number of ways.