TEN is the King of flatbed towing. So you have the attention of the right member.
No, not the "king" by far, limited by my equipment. But I have done it and it worked out well.
Some time ago I bought a car hauler trailer with the intention of pulling home a pre-'64 Compact in one trip. That hasn't happened yet, but I have put it to work. The trailer is about 18 feet with the center open, equipped with slide-out ramps, winch, and electric tongue jack.
My first trip was for the 1964 Airflyte. It was 160 miles form home, thirty-five years parked in the woods. The owner pulled it to the roadway and loaded it with his tractor's three-point hitch. It worked well with only the angle of the ramps being a problem. The tractor had to back onto the ramps a bit in order to place it far enough up onto the trailer. A few adjustments for clearance and a little jockeying, and it came off without a hitch...so to speak...
We loaded it backwards so that I could hook it off with the truck at the other end of the trip.
The camper had to sit up in order for the walls to clear the fenders of the hauler. The axle fit between, but the overall width didn't. The step was the hardest part to clear while loading it.
Tightly secured it rode home without any problems and with quite a few looks along the expressway.
The next adventure was a little more involved, a 1600-mile round trip solo mission retrieving the 1970 16SC. I had to load alone, and by the time I got there, I was finishing about 11:30 at night, trying to not keep the neighborhood awake.
The axle is a lot wider and would not fit between the fenders. I had to choose between leaving it behind or backing it over the fenders alone. I can't say I have ever been luckier, as it fell right where it had to be when it went off the fenders. A slight miss would have left the camper hanging helpless off the ends and would have meant jacking and blocking with no materials to do so all night. Once it was on the trailer, I couldn't get the hitch to release from the coupler. A bit of magic with the winch and a lot of sweating and it tied down for the trip home.
The 16SC is wider and it has more hanging under it, so clearance was an even bigger consideration. The outlet and the black tank barely cleared the fender. At some point, probably during loading, the tank struck the fender and blew out the top of the tank. Fortunately that was the only damage from the trip.
It's sure funny seeing those tail lights in the mirror, but you get used to it after 800 miles.
The last one I pulled home (on the trailer that is...) was a 1965? Pathfinder. It was a 55 mile trip from home, and is a lot lighter and smaller than the other two. This time it was my failing memory that was the tough part. I forgot the 2" hitch to load with. I almost left it but, believe it or not, my wife convinced me to keep trying. We found a couple old planks to run up the center and loaded it with the winch. The tongue jack had the wheel on it or it would not have worked. It went easily because it was so light. A trailer with the steel deck would not present this much of a challenge pulling on.
Tied down it never moved.
This trailer was narrow enough and nothing really hanging so clearance was not much of an issue, for a change. Unloading was just the opposite of loading, let it out easy with the winch with the trailer front end elevated and rolled 'er out on the grass.
Three things about pulling them this way. First, the phrase "properly secured". If you tie down properly with chains and binders as well as straps, and nothing is flapping in the breeze loose, which could blow off into traffic, you should never have any trouble with law enforcement, because that is the biggest issue so far as compliance with hauling laws.
Second, you will face a 95% chance that no matter how much you plan ahead, you will find some surprise problem loading, usually regarding clearances. It's something to do with "Murphy's Law", and boy if I ever get my hands on that Murphy.....
Third has to do with the question of wind resistance. You may be able to tell from the photos above that it does not matter which direction they are facing. Once you load them above the line of the box of the pickup (assuming you tow with a truck), their face or rear is directly in the wind. The 16SC was like towing a brick sail for 800 miles, and averaged 9 miles to the gallon all the way home.
Whatever you end up doing, remember to take time to get some photos along the way. It's fun to look back on any of these adventures. I've had too many that I didn't take photos, and sure do wish I had.