I always take exactly four. Except the one time the distinctive shape of Dublin Bay was visible earlier. I still don't know how I failed to recognize Stuttgart before.

I got London in 1, but otherwise same. If I've not actually been to the city, I generally can't do much better than "looks vaguely American", "looks vaguely central European", etc.

Yeah, I start there, try to find landmarks, which side of the road they drive on, where the rivers are, overall urban design (grid in Europe == new town/damaged in war?). Then if I still don’t have a clue, well, I can use distance to guesses to triangulate. Although that kinda feels like cheating.

My other issue is that at the 2nd and 3rd zoom level they all look smaller than they really are to me. Until I figured that out I spent minutes trying cities that aren't in the database...