Three full days is enough for most mid-sized cities, four to five for a large one like Tokyo, New York or Mexico City. The useful measure isn't sights per day — it's neighbourhoods: plan one or two a day and count how many the city has.
Attraction counts produce bad itineraries, because they encourage crossing a city four times a day. Neighbourhood counts produce good ones: pick two areas per day, walk between them, and accept that you'll miss things.
A flight that lands at 4pm doesn't give you a day, it gives you a dinner. When counting, count full days on the ground — a lot of "four-day" trips are really two and a half.