newtonian mechanics - Estimating atmospheric friction by measuring the change in velocity of a ball thrown straight upwards

Imagine I throw a ball straight upwards with some velocity $v_1$, and filming the ball with a camera, I can estimate a velocity $v_2$ (along the same vector) after the ball has moved a distance $D$. Using the difference between $v_1$ and $v_2$, and assuming constant friction due to air, how well can I estimate the initial velocity necessary to toss the ball some height $H$?

For fun - provided some $v_1$, $v_2$, and $D$, can we estimate an upper-bound for the Earth escape velocity with air friction/drag? Or is there unpredictable scaling of friction with velocity?