Can my F250 tow a Recreational Double? (What can my truck tow?)

Its been a while. Last time I posted here, I talked about hauling two utility trailers loaded with fire wood. I was told I needed an at least an F250 or 2500 class truck to do so. Well, now I have a 1996 F250, mileage on the truck is in the five digit figures and I had to take it in the repair shop, and the tow truck driver told me that I could probably tow one 6 X 12 utility trailer fully loaded, and I also had a 4 X 6 utility trailer that I thought about putting behind the 6 X 12, just because I have it. And I also asked the repair shop owner about whether or not, the F250 I have can tow a 26' or shorter fifth wheel, with a 6 X 12 utility trailer loaded with some stuff I was going to haul to an up north cabin up there, behind the fifth wheel, and the repair shop guy said that, in order to tow a recreational double, I would probably be best with an F350 or dually, however, my brother bought a 30' travel trailer that he towed behind a Ford F150 with no problems. My dad said my brother was probably taking chances.

So, my two questions are, 1.) If I choose to tow my 4 X 6 30'' high sides utility trailer with no brakes, behind a single axle 6 X 12 30'' high sides utility trailer with brakes, would that small of a trailer really mess with, and/or sway the 6 X 12 utility trailer? And 2.) Would my F250 tow a 28.6' or shorter fifth wheel and a 6 X 12 utility trailer, both trailers with brakes fully loaded with what I want to take up north? I just want a few more opinions on what my F250 might be able to haul. Both double trailer combinations are possibilities, depending on what my truck can tow. The two different utility trailers would be a double bumper pull, and the other combination would be a fifth wheel/bumper pull trailer combination.

Thanks for any answers.

You would be pushing it to tow double. And not with the trailer without brakes. Both trailers must have brakes. Start by checking your state DMV or DOT for particulars. Then check your manual and door tag for truck capacities. Its not what you can pull as much as it is how much you can stop. If you go over what is legal and end up in an accident you are liable even if the other guy was at fault because you were knowingly exceeding your safe limits.