I have hauled a 8N and other Ford series tractors for years using a 16' and a 18' car hauler. Both were 7,000# car haulers and it worked great.
On the 16' trailer I backed it on. My current 18' trailer I just pull it on forward. The 8N is not that heavy, right around 2,500# but can weigh about 4,000# with the rears filled. As for securing I used 4 chains and 2 boomers.
I put a tow pin in the draw bar and ran each of my short 10' chains to the corners of the trailer at aprox. 45deg angles. I like to use 2 short chains each independent of each other incase one fails or comes loose. I then idle the tractor up to stake up the slack then from the front brush guard I used 2 more 10' chains to the corners of the trailer again at aprox. 45deg angle and then used my 2 boomers to snug it down good.
If you are hauling any implements make sure you lower them to the trailers deck to take the load of they 3 point and secure them with a strap or chain over the top of them.
Drive a few miles and check everything. A stop about every 100 miles to get a drink, hit the rest room, check the load, check the trailer tires/bearings is a good idea also.
Chris