Just how short is it? "Short" comes in several sizes now, based on the combo of cab style (regular, extended or crew) and bed length (short or standard or long). A 2500 probably doesn't have the real short (5.5 ft) bed, but a regular cab standard (6.5 ft) bed is still considered a pretty short truck.
Basically you have to calculate the distance from pin to the back of the cab and compare to the width and swing radius of the particular trailer you choose. Generally speaking, a 5W has a strong potential to strike the rear of the cab in a sharp (jack-knife) turn if you aren't watching closely.