The terminal velocity of a quarter varies based on its orientation during free fall, with estimates suggesting it could reach around 30 to 40 mph when falling flat and potentially up to 100 mph when falling edge down. The time to reach this terminal velocity is typically less than 10 seconds, though it never fully achieves that speed due to gradual acceleration. The discussion references a practical experiment involving a quarter and a moving car to demonstrate terminal velocity by observing the angle of swing of the quarter when held out the window. Additionally, it notes that air resistance increases at lower altitudes, which could affect the terminal velocity if dropped from significant heights. Overall, the conversation highlights the complexities of calculating terminal velocity for a quarter and the factors influencing it.