I've towed a small boat and trailer around that weigh a little over 1k combined. I have a 4 speed w/O.D. and 3:90 gears. It does just fine, and being able to split 3rd and 4th helps immensly on the hills. Lower altitude helps. So does wind at your back. But you gotta face it, a 235 is going to struggle towing anything uphill. And as said before, good brakes can't be overstated.
I'm currently building a warmed 261 stroker that I'm expecting to do much better in that regard.


1962 Fleetside 4spd 235 w/O.D. posi 3:90
In the Stovebolt Gallery
1990 Subaru Legacy Wagon AWD 2.2 5sp
2013 Ram Tradesman C/V
My Webshot Photos]