the truck has bad *** brakes QUOTE]
no way dude, these trucks in no way shape or form have good brakes, IMO...
That being said, with trailer brakes, and a good controller, that are up to the task, braking shouldn't be a problem.
I've had a 3400lbs car on a 1500lbs trailor, plus 500~ lbs in the bed, plus two people in the cab, and the truck did fantastic towing. I did use a weight distributing hitch, which IMO is 100% necessary if you want to tow anything that weighs more than what the capasity of the bed is, which max is 1500lbs. The amount of stability and safety it provides is undeniable. WELL worth the investment.
As for the rear, semi floating bearings can be plenty durable - and aside from seal failures, I haven't seen anyone post here about bearing failures. The bearing design on the m226 is the same as just about every other dana 44 setup IIRC. The size of the bearing has a lot to do with how durable it is, as well as proper oil level in the axle. When I bought the last set of tires, I ended up getting the heavier higher rated tires for the simple fact that towing was a possibility.
To be honest though, I never intended to tow often, or more than 400 miles or so round trip. If I thought for a minute I would, I definately would have picked up a Titan or other full size truck. But for how often I tow, and the main purpose of the truck being commuting and driving around, getting a bigger vehicle was something I just didn't want to deal with.
So "cliffs"? keep the oil level at the proper height, use a quality oil, and air bags/weight distributing hitch, and I think you'll be fine.