I've had pretty good luck making trips with my '63 c10. The longest I did was from Beaumont, TX up to Southern MN to get some truck parts. I pulled a double axle trailer all the way up there. Once there, we loaded a 235 in the back of the truck and loaded a '48 1 ton minus cab and front clip onto the trailer. Drove it back, and had 0 problems on the whole trip.
However, I've owned the truck for 15 years, the 230 had been replaced by a 350, and the 3 speed by a 4 speed and then an nv4500. I still had drum brakes all the way around, but the hard lines had been completely replaced over the past 15 years (just whichever section had sprung a leak).
Regarding braking, just don't follow anyone close, engine brake, anticipate your stops, and give yourself plenty of room.
My experience with these old trucks is that they can reliably do just about anything a new truck can do just not as comfortably or as fast depending on your upgrades, and they look a heck of a lot better, are easier to maintain, and they're cheaper
