The 58-59 trucks were once considered the ugly ducklings of the Task Force series. In recent years they have gained in popularity, especially the short box fleetsides. With all of the current builders sourcing these trucks the prices are at a premium.
Will you have a chance to preview the truck prior to bidding? Pictures are great but they don't show everything going on. I would set your max bid where you are comfortable, you have fees and possibly shipping to consider as well.
Not many would be able to give you a set price without first really seeing the truck.