It all depends on the property you have, and what you will be using it for.
I currently am using a 1952 8N (the one in my pic). Bought it when I was 21 (9 years ago) for $1500. At our home, I brushhog around a 4 acre pond, a 2 acre pond, and a road that connects them. There is about 20-30 ft of grass around the ponds and road. I have a 1/2 acre plot, and 3-4 small micro plots (1/10ish acre). The 8n works awesome for all of the above. A bigger tractor with a bucket would not be able to maneuver the microplots because of the trees and shapes of the plots. I don't think I could even turn around in most of them. We also have a 650ft driveway that I plow with the 8n and backblade. Works flawlessly. The driveway is even somewhat elevated, and I have not had a problem with the 2wd going uphill with a load of snow on the back. The 8n is very light too. I can drive it around the yard and it doesn't sink in or tear the yard up. Since there is no power steering, the sharp turns are obsolete, so the front tires don't tear things up plus you get quite an upper body workout haha. Pulls the trailer with firewood, deer, ect with ease. For our house it works perfectly.
On the flipside, my dad had 80 acres up in Cheboygan that had a 10 acre field in the middle, and a lot of 1/2-1/4 acre foodplots. I originally bought the 8n for the property, but was very limited on how much we could do. Only had weekends in the summer to do plots, and its hard to do 8-10 acres total of plots with just an 8n. My dad eventually bought a 52 horse Kubota and a big disc, and the 8n was basically used to cut the roads.