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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