There are many things that always need to be thought out at first. However, the 23.5 sits low and not high on the trailer which is an important factor not to swaying as the center of gravity is low. If the trailer has brakes and/or brakes can be added to that axle, even better. There is also speed as well. I have pulled a Hunter 36 on a hydraulic trailer behind a pick up but again I went slow and had brakes using caution as always. Therefore, there are always many factors to consider but one is adding distance to acceleration and braking particular if there are no brakes on the trailer.