We have a 2001 F250 Superduty, Supercab, Short bed with a lift. The floor of the bed measures 40" from the ground, the top of the gunnels/sides of the bed measure at 60". We're looking to purchase a four horse head to head trailer, and are concerned that if we make a long distance purchase that the trailer won't fit safely. Any thoughts? Thanks! (this is also posted under trucks... hoping for thoughts from any and all!)

Since you're looking for some thoughts, here's mine...

A truck with a lift towing a significant trailer is just asking for trouble. That four horse trailer is about all that truck wants.
Your truck/trailer clearance will be an issue. Short bed too! Does the trailer nose taper? The stock drive shaft will be an issue at the joint ends. Stock tire or mudders? Check the load ratings on the sidewalls. A loaded four horse trailer is right at your truck's limits. you have very little margin.

To make a long distance purchase, ask the distance from the ground to the bottom of the neck-over... with the trailer level and on a level surface. That'll tell you how much clearance you'll have.