A lot of the answer to this question depends on what 5th wheel you end up buying. Most modern trailers (like the Montana we sell) are specifically designed to be towed with a standard bed pickup. (The term 'short' now refers to the small pickups with 5' beds..'standard' beds are the 6.5' models, and 'long' beds are the 8' models. You'll only find the 'short' beds on the 1/2 ton crew cab models.) The front caps and the pin boxes are designed to give maximum turning clearances while using the standard beds.
However, if you end up buying an older 5th wheel from the mid nineties, for example, you may have tremendous trouble towing it with that bed. On these trailers, the pin box is located back under the front of the trailer. So make sure the trailer you are looking at has the pin box pointed out in front of the trailer at least an inch or two, and you should be fine.
Casey
1995 K1500 Tahoe 2 door, 6.5LTD, 4L80E, NP241, 3.42's, 285/75R16 BFG K02's; 1997 506 block; Kennedy OPS harness, gauges, Quick Heat plugs, and TD-Max chip; Dtech FSD on FSD Cooler; vacuum pump deleted, HX35 turbo, Turbo Master, 3.5" Kennedy exhaust, F code intake; dual t/stats, HO water pump, Champion radiator; Racor fuel filter