Ideally, you need a "deckover" trailer rated for 10,000lbs GVWR minimum to haul an M-size tractor with the wheels dished out. These are either 96" or 102" wide and have the wheels underneath instead of on the sides.
The problem with a deckover is the tractor is way up high, and that can bother some people. Properly loaded and strapped down it's a non-issue.
If all you can find is the "car hauler" type trailer with the deck between the wheels, you will need to flip one of the wheels around on the M so it's dished in. The maximum distance between the fenders on a car hauler is 83". I've never seen one with any more than that. The minimum width you can get on an M with the wheels dished out is 84" IIRC. If you've got a trailer with removeable fenders, you can squeeze through and put the fenders back on. Otherwise you're flipping a wheel.
The car hauler type trailer puts the load much closer to the ground. They are more stable.
As for towing with the 1/2 ton, that will depend on where you're going and how far you're going. If it's less than 100 miles, and you don't mind sticking to back roads, just take it slow and easy. At 30 miles an hour it'll take you a while but you'll get there in one piece. Heck, you might find that it tows so well that you can even go a little faster and make some time. Just don't get in a hurry.
Make sure the trailer brakes work. You will need them because a 1/2 ton doesn't have adequate braking for 5000lbs of tractor and 2000lbs of trailer, AND it's illegal in most states to tow a trailer rated for more than 2999lbs without brakes.
Using my 2003 1/2 ton Chevy, I towed a Super A with 1000 loader, weights on all four wheels, loaded tires, about 20 miles on a U-haul car hauler trailer. That was about 4000lbs on a 2500lb trailer. I wouldn't want to do it for a living, but it worked fine for the short distance. I was able to drive the speed limit, up to 55MPH, all the way home, though most of the way was 35-40MPH.
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Today's Featured Article - Identifying Tractor Noises - by Curtis Von Fange. Listening To Your Tractor : Part 3 - In this series we are continuing to learn the fine art of listening to our tractor in hopes of keeping it running longer. One particularly important facet is to hear and identify the particular noises that our
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