Towing with 5.5 Ft Box

The OP does not say what truck, and a 5.5 bed length would not be a good choice for a FW. While many 1/2 ton trucks, such as the one 2112 has, are capable of towing some FWs. The so called 1/2 ton towable FWs normally have a GVWR of 10K or less and can be towed with the properly equipped 1/2 ton truck. I don't think you can get a properly equipped truck with 5.5 bed.

Yes, the newer model 1/2 T Ford trucks have great brakes.

Jerry