The length and modulus of the strings (identical material, I assume) will affect the result, as well as the 'speed' and force applied. A helpful model would be to treat the strings as springs and the Spring - mass - spring - support would have different natural modes of oscillation. I don't think the calculations would be that hard to do (you'd need a bit of motivation). First write an equation of motion and solve it for the conditions. In the end, it's coupled oscillators. For a slowly applied force, the result will always be that the top string will break, of course.