This is one of those problems where it helps to be careful about the distinction between force and mass. It's also easier to get it right if you use the metric system because the distinction between mass (in kilograms) and force (in Newtons, and the gravitational force on a 1 kilogram mass is ##9.8 \approx 10## Newtons) is explicit - American units blur the two concepts together with the word "pound".
So I'll restate it in metric units and I'll bet that you can work it out for yourself: does a 100 kilogram object subjected to an upward force of 250 Newtons (the gravitational force on a 25 kilogram object) accelerate downwards more or less quickly than a 75 kilogram object in free fall? Calculate the net force on each, plug into ##F=ma##, see what comes out.