CC, I'm not surprised you've been towing for 50 years. Like I said in my post above, you're a little behind the times. Since we're comparing resumes... I've worked at a Ford dealership since the 1980's, currently own 5 trailers (everything from boats, to a flatbed, to the above travel trailer as well as a fifth wheel camper). I have personally owned numerous Ford trucks from a Ranger to F-150's to my current 6.7L Powerstroke.
To give you an idea of what I am talking about... Your 1999 F-350 Powerstroke, even if it was a dually, is only rated at 10,000 max trailer towing for bumper pull (which is what we are talking about here). A new F-150 4x4 CC is rated at 11,600 and can be configured to 12,200. The weight of a Super Duty is nice in windy situations, but from somebody that has personally owned a 2006 F-150 and a 2010 F-150, I can tell you that the gyroscopic anti-sway devices included in the newer trucks would blow your mind as far as the ability to control the truck in poor conditions or while passing semi's.
PS. I have never broken down, never done damage to a vehicle, in fact I could've welded all my hoods shut except for regular oil changes. To tow any trailer, a guy needs to know what he is doing... but if a guy can't tow a 10,000 trailer with a new F-150, that's on him. Not the truck.