I am doing a little research for someone. They have a 1995 F-150 with the 4.9L (300 inline 6) and manual transmission. They are trying to decide if it will pull a 24 foot enclosed trailer with a Ford 8N tractor and a Fordson both loaded inside. Total weight of tractors, trailer and riders would be about 9000 lbs. They plan on pulling this at least once, and probably a few (very few) times after that in Kansas (read = flat). Are they nuts, or would this be possible. We tried reading in the manual, but decided that we were mathmatically challenged.
Having had a 4.9l back in the day, I would not hesitate to pull that as long as the load is balanced and trailer has its own brakes.
I pulled a 3500# horse trailer,with two horses, up some scarey steep grades.
The mid 90s series F150s were not recommended for extended towing of more than 5,000#, this was from the Ford Truck Owners Bible and Trailer Life Magazine. That was assuming you had the tow package and the heavier engine and tranny combo etc.
9,500# is a pretty hefty load. The Inline 6 is a good engine but if I recall, that combo was usually not rated for anything like 5,000#. The 6 was usually an economy model, not a tow vehicle. I could be wrong, check your door sticker and manual to be sure. Look for GCWR and GVWR and GAWR rating. Probably the most important one is GCWR, Gross Combined Weight Rating, this is truck and trailer with full loads.
Assuming you are over rating, it would be illegal for you to tow the weight you plan. If you have an accident you will be held to blame. While you probably could physically do so, you would be pushing the safety margins by a fair amount and you will increase the wear and tear on your vehicle.
The biggest weaknesses on your model if I recall are brakes, tranny, axle and a few other things. If you get into a panic stop situation, I would not want to be the person in front or to the side of you. You probably will be OK, but your risk is higher.
I believe you have the M5OD tranny. That is a weak tranny for towing I have read. If you do tow, use 4th gear since I have read on this site that the 5th gear power flow pathway is weak and will damage the tranny.
You can tow almost anything with almost any vehicle, but that doesn't mean it is legal and more importantly safe.
I have a very similar truck that I tow with and can tell you it will be no fun. I tow a car on a 20' open trailer that weighs approx 6500 total. It can tow decent on the flat but takes forever to accel and will lose speed (alot) in any sort of hill. Your setup with the extra frontal area of the enclosed trailer and extra weight will truely suck. If you were going 20 miles, id say go for it. (assuming propper weight dist and good brakes). Anything more than that is going to be real rough on that truck.