It sure was easy with an empty trailer.
It appears to be about 10" in diameter and @ 100psi of air that would give roughly 11,000lbs of force. But hydraulics are positive displacement. The fluid wont compress, which means hydraulics will raise just as fast under load as empty.
Look at the volume of air required to fill that bladder with 100psi. How long would it take your air compressor to fill a tank that size to 100psi??? I am guessing longer than if it were a hydraulic trailer. That trailer with 7k on it looks like it would raise pretty slow to me.