The longer the trailer the easier it is to back up.....all you need is maneuvering room in front of the truck to turn and swing things into place. I have a 6500 lb. 30 ft. trailer I pull with my Silverado 1500, 5.8 liter 3:42 geared 6 speed trans with 1666 payload and do so with no problems. If you stick with the ultra light models then you can tow it safely with what you have. Length is not that big an issue really if you stay with in you weight limits. Your truck needs to be in good mechanical condition with good load range E tires. Get the floor plan that works for you. That is the most important factor IMO or you will be trading it in after the first year when you find it doesn't fit your needs....and take a beating on the depreciation. Save your money for a new truck and get the trailer that works for you.