For every option you describe, you are a looking at a Super MTA diesel as the oldest IH tractor to have all those things available (probably looking at near $10,000 for a good one).
A 560 diesel will fit your trailer weight wise, I don't know about the width of your trailer, though. You may have to narrow it up a bit to fit on there.
Beyond the 560 diesel you would be looking at a 504 diesel, 544 diesel, maybe a 656, 666, or 686 diesel.
For the best bang for the buck, I would personally go with a nice 560 diesel. You should be able to get a good one for around $5000 or so.
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Today's Featured Article - The 8N and the Fox - by Zane Sherman. Dec. 13 1998, Renfroe, Alabama. Last niht I dreamed about the day that I plowed the field of about 10 acres over on what Jimmy and Dandy called the Ledbetter field. I was driving the 1948 8N Ford tractor that Jimmy bought in 48 new This was prebably in about 1951 and maybe even befor the house was built. This would have made me to be about16 years old and I drove the tractor for nothing and would have paid to drive it if I had had any money which I didn't, but neit
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